N-sulphonyl and N-sulphinyl phenylglycinamide

ABSTRACT

Novel α-amino acid amides of formula (I) as well as possible isomers and mixtures of isomers thereof, wherein the substituents are defined as follows: n is the number zero or one; R 1  is optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl; or a group NR a R b  wherein R a  and R b  are each independently of the other hydrogen, alkyl or form together an alkylene bridge; R 2  is hydrogen or alkyl; R 3  is optionally substituted aryl or heteroaryl; A is alkylene; and B is optionally substituted aryl; with the exception of the following compounds 2-phenyl-N-(1-phenyl-ethyl)-2-(4-methylphenyl)-sulfonylamino-acetamide, 2-phenyl-N-(1-phenyl-ethyl)-2-(4-chlorophenyl)-sulfonylamino-acetamide, 2-phenyl-N-(1-phenyl-ethyl)-2-(4-nitrolphenyl)-sulfonylamino-acetamide, 2-phenyl-N-(1-phenyl-ethyl)-2-(4-methoxyphenyl)-sulfonylamino-acetamide, 2-phenyl-N-(1-phenyl-ethyl)-2-(4-fluorophenyl)-sulfonylamino-acetamide, 2-phenyl-N-(1-phenyl-ethyl)-2-phenyl-sulfonylamino-acetamide and 2-phenyl-N-(1-phenyl-ethyl)-2-methane-sulfonylamino-acetamide. The novel compounds have plant-protective properties and are suitable for protecting plants against infestations by phytopathogenic microorganisms, in particular fungi.

This application is a 371 of international application PCT/EP99/01216, filed Feb. 25, 1999.

The present invention relates to novel α-amino acid amides of formula I below. It relates to the preparation of those substances and to agrochemical compositions that comprise at least one of those compounds as active ingredient. The invention also relates to the preparation of the said compositions and to the use of the active ingredients or the compositions in the control or prevention of plant infestation by phytopathogenic microorganisms especially fungi.

The compounds according to the invention correspond to the general formula I

as well as possible isomers and mixtures of isomers thereof,

wherein the substituents are defined as follows:

n is the number zero or one;

R₁ is optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl; or a group NR_(a)R_(b) wherein R_(a) and R_(b) are each independently of the other hydrogen, alkyl or form together an alkylene bridge;

R₂ is hydrogen or alkyl;

R₃ is optionally substituted aryl or heteroaryl;

A is alkylene; and

B is optionally substituted aryl;

with the exception of the following compounds

2-phenyl-N-(1-phenyl-ethyl)-2-(4-methylphenyl)-sulfonylamino-acetamide,

2-phenyl-N-(1-phenyl-ethyl)-2-(4-chlorophenyl)-sulfonylamino-acetamide,

2-phenyl-N-(1-phenyl-ethyl)-2-(4-nitrophenyl)-sulfonylamino-acetamide,

2-phenyl-N-(1-phenyl-ethyl)-2-(4-methoxyphenyl)-sulfonylamino-acetamide,

2-phenyl-N-(1-phenyl-ethyl)-2-(4-fluorophenyl)-sulfonylamino-acetamide,

2-phenyl-N-(1-phenyl-ethyl)-2-phenyl-sulfonylamino-acetamide and

2-phenyl-N-(1-phenyl-ethyl)-2-methane-sulfonylamino-acetamide.

The above alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl or heteroaryl groups may carry one or more identical or different substituents. Normally not more than five substituents in each of these groups are present at the same time. Examples of substituents of these groups are: alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, phenyl and phenylalkyl, it being possible in turn for all of the preceding groups to carry one or more identical or different halogen atoms; alkoxy; alkenyloxy; alkynyloxy; alkoxyalkyl; haloalkoxy; alkylthio; haloalkylthio; alkylsulfonyl; formyl; alkanoyl; hydroxy; halogen; cyano; nitro; amino; alkylamino; dialkylamino; carboxy; alkoxycarbonyl; alkenyloxycarbonyl; alkynyloxycarbonyl.

In the above formula I, “halogen” includes fluorine, chlorine, bromine and iodine, preferably fluorine, chlorine or bromine.

The alkyl, alkenyl and alkynyl radicals may be straight-chain or branched, this applying also to the alkyl, alkenyl or alkynyl moiety of other groups containing alkyl, alkenyl or alkynyl.

Depending on the number of carbon atoms mentioned, alkyl on its own or as part of another substituent is to be understood as meaning, for example, methyl, ethyl, propyl, butyl, pentyl, n-hexyl, n-heptyl, n-octyl, n-decyl, n-dodecyl and the isomers thereof, such as isopropyl, isobutyl, tert-butyl, sec-butyl, tert-amyl, 1-ethyl-hexyl, n-octyl, n-nonyl or n-decyl. Cycloalkyl denotes, depending on the number of carbon atoms mentioned, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl.

Alkenyl will be understood as meaning straight-chain or branched alkenyl such as allyl, vinyl, methallyl, 1-methylvinyl, but-2-en-1-yl, pent-2-en-1-yl or hex-2-en-1-yl. Preferred alkenyl radicals contain 3 to 4 carbon atoms in the chain.

Alkynyl can likewise, in accordance with the number of carbon atoms, be straight-chain or branched and is typically propargyl, but-2-yl-1-yl, but-1-yn-3-yl, pent-2-yn-1-yl or hex-2-yn-1-yl. The preferred meaning is propargyl.

A haloalkyl group may have one or more (identical or different) halogen atoms, such as, for example, CHCl₂, CH₂F, CCl₃, CClF₂, CH₂Cl, CHF₂, CF₃, CH₂CH₂Br, CH₂CF₃, CH₂CH₂F, C₂Cl₅, CH₂Br, CHBrCl, CH₂CH₂CF₃ etc.

Alkoxy is typically methoxy, ethoxy, propyloxy, isopropyloxy, n-butyloxy, isobutyloxy, sec-butyloxy and tert-butyloxy. Methoxy and ethoxy are preferred.

Alkylthio is typically methylthio or ethylthio.

Haloalkoxy is any alkoxy substituted with one or more halogen atoms. Typical examples are difluoromethoxy, trifluoromethoxy, 2,2,-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy and 2,2-difluoroethoxy.

Aryl can be for example phenyl or naphthyl.

Arylalkyl can be for example benzyl, 2-phenyl-ethyl or 3-phenyl-propyl.

Heteroaryl stands for aromatic ring systems comprising mono-, bi- or tricyclic systems wherein at least one oxygen, nitrogen or sulfur atom is present as a ring member. Examples are furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, tetrazinyl, indolyl, benzothiophenyl, benzofuranyl, benzimidazolyl, indazolyl, benzotroazolyl, benzothiazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, phthalazinyl, quinoxalinyl, quinazolinyl, cinnolinyl and naphthyridinyl.

Alkanoyl is, in accordance with the number of carbon atoms embraced, either straight-chain or branched. Typical examples are formyl, acetyl, propionyl, butyryl or pivaloyl.

As a result of the presence of at least one asymmetric carbon atom and/or at least one asymmetric sulfur atom in the compounds of formula I the compounds may occur in the form of optical isomers. Owing to the presence of an aliphatic —C═C— double bond, geometrical isomerism may also occur. Formula I is intended to encompass all of those possible isomeric forms and mixtures thereof.

Preference is given to compounds of formula I wherein

n is the number zero or one;

R₁ is C₁-C₁₀alkenyl, C₂-C₁₀alkenyl, C₂-C₁₀alkynyl, C₃-C₈cycloalkyl, C₃-C₈cycloalkyl-C₁-C₆alkyl,

C₆-C₁₀aryl, or C₆-C₁₀aryl-C₁-C₆alkyl that are optionally mono- or poly-substituted by C₁-C₈alkyl, C₁-C₈alkoxy, C₁-C₈alkylthio, C₁-C₈alkylsulfonyl, C₃-C₈cycloalkyl, C₁-C₈alkoxycarbonyl, C₃-C₈alkenyloxycarbonyl, C₃-C₈alkynyloxycarbonyl, C₃-C₈cycloalkyl-C₁-C₆alkyl, C₂-C₈alkenyl, C₂-C₈alkynyl, C₃-C₈alkenyloxy, C₃-C₈alkynyloxy, C₁-C₈alkanoyl (where all these alkyl, alkenyl, alkynyl or cycloalkyl containing groups may be partially or fully halogenated), halogen, cyano or nitro; or a group NR_(a)R_(b), wherein R_(a) and R_(b) are each independently of the other hydrogen, C₁-C₈alkyl or together are C₂-C₇alkylen;

R₂ is hydrogen or C₁-C₈alkyl;

R₃ is phenyl, naphthyl or heteroaryl formed by 1 or 2 five- or six-membered rings containing 1 to 4 identical or different heteroatoms selected from oxygen, nitrogen or sulfur and are optionally mono- or poly-substituted by C₁-C₈alkyl, C₂-C₈alkenyl, C₂-C₈alkynyl, C₁-C₈alkoxy, C₁-C₈alkylthio, C₁-C₈alkylsulfonyl, C₃-C₈cycloalkyl, C₃-C₈cycloalkyl-C₁-C₆alkyl, C₁-C₄alkylendioxy, C₁-C₈alkoxycarbonyl, C₃-C₈alkenyloxycarbonyl, C₃-C₈alkynyloxycarbonyl, C₃-C₈cycloalkyloxy, C₃-C₈alkenyloxy, C₃-C₈alkynyloxy, C₁-C₈alkanoyl, C₁-C₈dialkylamino, C₁-C₈alkylamino (where all these alkyl alkenyl, alkynyl or cycloalkyl containing groups may be partially or fully halogenated), halogen, nitro, cyano, hydroxy or amino;

A is C₁-C₈alkylen; and

B is phenyl optionally mono- or poly-substituted by C₁-C₈alkyl, C₂-C₈alkenyl, C₂-C₈alkynyl, C₁-C₈alkoxy, C₁-C₈alkylthio, C₁-C₈alkylsulfonyl, C₃-C₈cycloalkyl, C₃-C₈cycloalkyl-C₁-C₆alkyl, C₁-C₈alkoxycarbonyl, C₃-C₈alkenyloxycarbonyl, C₃-C₈alkynyloxycarbonyl, C₃-C₈cycloalkyloxy, C₃-C₈alkenyloxy, C₃-C₈alkynyloxy, C₁-C₈alkanoyl, C₁-C₈dialkylamino, C₁-C₈alkylamino, C₆-C₁₀aryloxy, C₆-C₁₀aryl-C₁-C₆alkoxy, C₆-C₁₀aryl-C₁-C₆alkenyloxy, C₆-C₁₀aryl-C₁-C₆alkynyloxy, C₁-C₈alkanoyloxy (where all these alkyl alkenyl, alkynyl or cycloalkyl containing groups may be partially or fully halogenated and where all aryl containing groups may be optionally mono- or poly-substituted by C₁-C₈alkyl, C₂-C₈alkenyl C₃-C₈cycloalkyl, C₁-C₈alkoxy, C₁-C₈alkylthio, C₁-C₈alkoxycarbonyl C₁-C₈halogenalkyl, C₁-C₈halogenalkoxy, C₁-C₈halogenthioalkyl, halogen nitro or cyano), halogen, nitro, cyano, hydroxy, amino or the phenyl group may be substituted in two adjacent positions by C₁-C₄alkylenedioxy wherein the alkylene part may be substituted by halogen (sub-group A).

Within the scope of sub-group A, special mention should be made of those compounds of formula I wherein

n is the number zero or one;

R₁ is C₁-C₁₀alkyl C₂-C₁₀alkenyl, C₃-C₈cycloalkyl that are optionally mono- or poly-substituted by C₁-C₈alkyl, C₁-C₈alkoxy, C₁-C₈alkylthio, C₁-C₈alkanoyl, C₁-C₈alkoxycarbonyl, C₁-C₈halogenalkyl, C₁-C₈halogenalkoxy, C₁-C₈halogenalkylthio, halogen, nitro or cyano; or a group NR_(a)R_(b), wherein R_(a) and R_(b) are each independently of the other hydrogen, C₁-C₈alkyl, or together are tetramethylene or pentamethylene;

R₂ is hydrogen or methyl;

R₃ is phenyl, naphthyl, furyl, thienyl, imidazolyl, thiazolyl, oxazolyl, pyridyl, pyrimidinyl, benzothiophenyl, benzothiazolyl, chinolinyl, pyrazolyl, indolyl, benzimidazolyl or pyrrolyl optionally substituted by 1 to 3 substituents selected from C₁-C₈alkyl, C₂-C₈alkenyl, C₃-C₈cycloalkyl, C₁-C₈alkoxy, C₁-C₈alkylthio, C₁-C₈alkoxycarbonyl, C₁-C₈halogenalkyl, C₁-C₈halogenalkoxy, C₁-C₈halogenalkylthio, halogen, hydroxy, nitro or cyano;

A is C₁-C₄alkylen; and

B is phenyl optionally substituted by 1 to 3 substituents selected from C₁-C₈alkyl, C₁-C₈alkoxy, C₃-C₈alkenyloxy, C₃-C₈alkynyloxy, phenyl-C₁-C₆alkyloxy, phenyl-C₃-C₆alkenyloxy, phenyl-C₃-C₆alkynyloxy, C₁-C₈alkylthio, C₁-C₈alkoxycarbonyl, C₁-C₈halogenalkoxy, C₃-C₈halogenalkenyloxy, halogen, hydroxy, nitro or cyano (where all phenyl containing groups may be optionally substituted by 1 to 3 substituents selected from C₁-C₈alkyl, C₁-C₈alkoxy, C₁-C₈alkylthio, C₁-C₈halogenalkyl, C₁-C₈halogenalkoxy, C₁-C₈halogenthioalkyl, halogen or cyano) (sub-group B).

An important group is formed by compounds of formula I wherein

n is the number one;

R₁ is C₁-C₆alkyl, C₂-C₁₀alkenyl, C₅-C₆cycloalkyl, that are optionally mono- or poly-substituted by C₁-C₈alkyl, C₁-C₈alkoxy, C₁-C₈alkoxycarbonyl, C₁-C₈halogenalkyl, C₁-C₈halogenalkoxy, halogen or cyano; or a group NR_(a)R_(b), wherein R_(a) and R_(b) are each independently of the other methyl or ethyl;

R₂ is hydrogen;

R₃ is phenyl optionally substituted by 1 to 3 substituents selected from C₁-C₈alkyl, C₂-C₈alkenyl, C₃-C₈cycloalkyl, C₁-C₈alkoxy, C₁-C₈alkylthio, C₁-C₈alkoxycarbonyl, C₁-C₈halogenalkyl, C₁-C₈halogenalkoxy, C₁-C₈halogenthioalkyl, halogen, hydroxy, nitro or cyano;

A is ethylen; and

B is phenyl optionally substituted by 2 to 3 substituents selected from C₁-C₈alkyl, C₁-C₈alkoxy, C₃-C₈alkenyloxy, C₃-C₈alkynyloxy, phenyl-C₁-C₆alkyloxy, phenyl-C₃-C₆alkenyloxy, phenyl-C₃-C₆alkynyloxy, C₁-C₈alkylthio, C₁-C₈alkoxycarbonyl, C₁-C₈halogenalkoxy, C₃-C₈halogenalkenyloxy, halogen, hydroxy, nitro or cyano (where all phenyl containing groups may be optionally substituted by 1 to 3 substituents selected from C₁-C₈alkyl, C₁-C₈alkoxy, C₁-C₈alkylthio, C₁-C₈halogenalkyl, C₁-C₈halogenalkoxy, C₁-C₈halogenthioalkyl, halogen or cyano) (sub-group C).

A special group within the scope of sub-group C comprises compounds of formula I wherein

n is the number one;

R₁ is C₁-C₄alkyl optionally mono- or poly-substituted by fluorine, chlorine, bromine or dimethylamin;

R₂ is hydrogen;

R₃ is phenyl optionally substituted by 1 to 3 substituents selected from C₁-C₈alkyl, C₂-C₈alkenyl, C₃-C₈cycloalkyl, C₁-C₈alkoxy, C₁-C₈alkylthio, C₁-C₈alkoxycarbonyl, C₁-C₈halogenalkyl, C₁-C₈halogenalkoxy, C₁-C₈halogenthioalkyl, halogen, nitro or cyano;

A is ethylen; and

B is a group

 wherein

R₈ is C₁-C₄alkyl, and

R₉ is C₁-C₈alkyl, C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl-C₁-C₆alkyl, phenyl-C₃-C₆alkenyl, phenyl-C₃-C₆alkynyl, C₁-C₈halogenalkyl, C₃-C₈halogenalkenyl (where all phenyl containing groups may be optionally substituted by 1 to 3 substituents selected from C₁-C₈alkyl, C₁-C₈alkoxy, C₁-C₈alkylthio, C₁-C₈halogenalkyl, C₁-C₈halogenalkoxy, C₁-C₈halogenthioalkyl, halogen or cyano) (sub-group Ca).

Certain α-amino acid derivatives having a different kind of structure have already been proposed for the control of plant-destructive fungi (for example in EP-398 072, EP-425925, DE-40 26 966, EP-477 639, EP-493 683, DE-40 35 851, EP-487 154, EP-496239, EP-550 788 and EP-554729). Those compositions are not, however, satisfactory in their action. Surprisingly, with the compound structure of formula I, new kinds of microbicides having a high activity have been found.

DESCRIPTION OF THE PROCESS FOR THE PREPARATION OF COMPOUNDS ACCORDING TO THE INVENTION

The compounds of formula I can be prepared by one of the following processes:

Step B: An amino acid of formula II or a carboxy-activated derivative of an amino acid of formula II, where R₁, n, R₂ and R₃ have the meaning as defined above, is reacted with an amine of the formula V where A and B have the meaning as defined above, optionally in the presence of a base and optionally in the presence of a diluting agent.

Any carboxy-activated derivatives are suitable as carboxy-activated derivatives of the amino acid of formula II, such as acid halides, for example acid chlorides or fluorides; symmetrical or mixed anhydrides, for example the mixed O-alkylcarboxylic acid anhydrides; activated esters, for example p-nitrophenyl esters or N-hydroxysuccinimide esters, and activated forms of the amino acid II produced in situ using condensation agents (e.g. dicyclohexylcarbodiimide, carbonyldiimidazole, O-(benzotriaz-1-yl)-N,N,N′,N′-bis(pentamethylene)uronium hexafluorophosphate, O-(benzotriaz-1-yl)-N,N,N′,N′-bis(tetramethylene)uronium hexafluorophosphate, (benzotriazol-1-yloxy)-tripyrrolidinophosphonium hexafluorophosphate, (benzotriazol-1-yloxy)-tris(dimethylamino)phosphonium hexafluorophosphate or O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate).

The acid halides corresponding to the amino acid of formula II can be prepared by reacting the amino acid of formula II in a manner known per se with a halogenating agent, for example phosphorus pentachloride, thionyl chloride, oxalyl chloride, cyanuric fluoride or diethylaminosulfur trifluoride.

The mixed anhydrides corresponding to the amino acid of formula II can be prepared by reacting the amino acid of formula II with chloroformic acid esters, for example chloroformic acid alkyl esters preferably chloroformic acid isobutyl ester, in the absence or presence of an acid-binding agent, such as an inorganic or organic base, for example a tertiary amine, e.g. triethylamine, pyridine, N-methylpiperidine or N-methylmorpholine.

Step A: The compounds of formula II can be prepared by reaction of an amino acid of formula IV where R₂ and R₃ have the same meanings as defined above with a sulfonyl halide or a sulfinyl halide of formula III where R₁ and n have the meanings as defined above and where X is halide, preferentially chlorine or bromine. The reaction is optionally performed in a solvent and in presence of a base.

Step C: The compounds of formula I can also be prepared by reaction of an amino acid derivative of formula VI where R₂, R₃, A and B have the same meanings as defined above with a sulfonyl halide or a sulfinyl halide of formula III where R₁ and n have the same meanings as defined above and where X is halide, preferentially chlorine or bromine. The reaction is performed in the same manner as described for step A.

c) The compounds of the formula I, wherein n is 1 can be prepared by oxidizing compounds of formula I wherein n=0 (I′) with organic oxidizing agents, such as alkyl hydroperoxides, for example cumyl hydroperoxide, and inorganic oxidizing agents, such as peroxides, for example hydrogen peroxide, or transition metal oxides, for example chromium trioxide, and transition metal oxide salts, for example potassium permanganate, potassium or sodium dichromate, are suitable oxidizing agents.

The reaction of the compounds of formula I′ with the oxidizing agents takes place in an inert diluent, such as water or a ketone, for example acetone, or in mixtures thereof, in the absence or presence of an acid or in the absence or presence of a base, at temperatures of from −80 to +150° C.

The compounds of formula VI can be prepared by the following process d)

Step D: An isocyanide of formula VII, where A and B are as defined before (see D.Seebach, G.Adam, T.Gees, M.Schiess, W.Weigang, Chem.Ber.,1988,121,507) is reacted with a known compound of formula VIII (R₂ and R₃ are as defined before), a known compound of formula IX (R₁₀ is lower alkyl or H) and ammonia in a solvent (typically an alcohol as methanol or ethanol, tetrahydrofuran, methylenchloride) at a temperature between −20° and +150° C., optionally in the presence of a Lewis acid, typically ZnCl₂ (Ugi reaction).

Step E: A compound of formula X, where R₂, R₃, R₁₀, A and B are as defined before, is hydrolysed under acidic or basic conditions at a temperature between 0° and 100° C. Typical acids are mineral acids as HCl, H₂SO₄, organic acids as p-toluenesulfonic acid, methanesulfonic acid, trifluoroacetic acid; typical bases are NaOH, KOH, Ba(OH)₂, carbonates, triethylamine, ethyl diisopropylamine; typical solvents are alcohols like ethanol or methanol, tetrahydrofurane, dimethylformamide, dimethylsulfoxide.

Compound VI can be converted to compounds of formula I by step C as described under process b).

The invention relates also to the amino acid derivatives of formula VI, wherein R₂, R₃, A and B have the meaning as defined for formula I.

The sulfonic acid or sulfinic acid or the sulfonic or sulfinic acid derivative of formula III required for process a) or b) and the amino acids of formula IV required for process a) are known per se.

Suitable sulfonic or sulfinic acid derivatives of formula III are any compounds wherein Z is a leaving group, such as sulfonic acid halides or sulfinic acid halides, e.g. sulfochlorides or sulfinic acid chlorides; symmetrical or mixed anhydrides; and activated forms of sulfonic acid or sulfinic acid produced in situ using condensation agents, such as dicyclohexylcarbodiimide or carbonyldiimidazole.

Surprisingly, it has now been found that compounds of formula I have for practical purposes a very advantageous biocidal spectrum in the control of phytopathogenic microorganisms, especially fungi. They possess very advantageous curative and preventive properties and are used in the protection of numerous crop plants. With the compounds of formula I it is possible to inhibit or destroy pests occurring on various crops of useful plants or on parts of such plants (fruit, blossom, leaves, stems, tubers, roots), while parts of the plants which grow later, for example, also remain protected against phytopathogenic fungi. The novel compounds of formula I prove to be preferentially effective against specific genera of the fungus class Fungi imperfecti (e.g. Cercospora), Basidiomycetes (e.g. Puccinia) and Ascomycetes (e.g. Erysiphe and Venturia) and especially against Oomycetes (e.g. Plasmopara, Peronospora, Bremia, Pythium, Phytophthora). They therefore represent in plant protection a valuable addition to the compositions for controlling phytopathogenic fungi. The compounds of formula I can also be used as dressings for protecting seed (fruit, tubers, grains) and plant cuttings from fungal infections and against phytopathogenic fungi that occur in the soil.

The invention relates also to compositions comprising compounds of formula I as active ingredients, especially plant-protecting compositions, and to the use thereof in the agricultural sector or related fields.

In addition, the present invention includes the preparation of those compositions, wherein the active ingredient is homogeneously mixed with one or more of the substances or groups of substances herein described. Also included is a method for the treatment of plants which comprises applying the novel compounds of formula I or the novel compositions.

Target crops to be protected within the scope of this invention comprise, for example, the following species of plants: cereals (wheat, barley, rye, oats, rice, maize, sorghum, spelt, triticale and related species); beet (sugar beet and fodder beet); pomes, stone fruit and soft fruit (apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries and blackberries); leguminous plants (beans, lentils, peas and soybeans); oil plants (rape, mustard, poppy, olives, sunflowers, coconut, castor oil plants, cocoa beans and ground-nuts); cucumber plants (marrows, cucumbers and melons); fibre plants (cotton, flax, hemp and jute); citrus fruit (oranges, lemons, grapefruit and mandarins); vegetables (spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes and paprika); lauraceae (avocados, cinnamon and camphor) and plants such as tobacco, nuts, coffee, sugar cane, tea, pepper, vines, hops, bananas and natural rubber plants, and also ornamentals.

The compounds of formula I are normally applied in the form of compositions and can be applied to the area or plant to be treated simultaneously or in succession with further active ingredients. Those further active ingredients may be fertilizers, micronutrient donors or other preparations that influence plant growth. It is also possible to use selective herbicides, and insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of those preparations, if desired together with further carriers, surfactants or other application-promoting adjuvants customarily employed in formulation technology.

Suitable carriers and adjuvants may be solid or liquid and correspond to the substances ordinarily employed in formulation technology, such as, e.g. natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binding agents or fertilizers. Such carriers are for example described in WO 97/33890.

A preferred method of applying a compound of formula I, or an agrochemical composition comprising at least one of those compounds, is application to the foliage of the plants (foliar application), the frequency and the rate of application depending upon the risk of infestation by the pathogen in question. The compounds of formula I may also be applied to propagation material (grains, fruits, tubers, shoots, cuttings, roots etc.) (dressing), for example either by impregnating cereal grains (seeds) or potato tubers or freshly cut shoots with a liquid formulation of the active ingredient or by coating them with a solid formulation.

The compounds of formula I are used in unmodified form or, preferably, together with the adjuvants conventionally employed in formulation technology, and are for that purpose advantageously formulated in known manner e.g. into emulsifiable concentrates, coatable pastes, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granules, and also encapsulations in e.g. polymer substances. As with the nature of the compositions, the methods of application, such as spraying, atomizing, dusting, scattering, coating or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances.

Advantageous rates of application are normally from 1 g to 2 kg of active ingredient (a.i.) per hectare, preferably from 10 g to 1 kg a.i./ha, especially from 25 g to 750 g a.i./ha. When used as seed dressings, rates of from 0.001 g to 1.0 g of active ingredient per kg of seed are advantageously used.

The formulations, i.e. the compositions, preparations or mixtures comprising the compound (active ingredient) of formula I and, where appropriate, a solid or liquid adjuvant, are prepared in known manner, e.g. by homogeneously mixing and/or grinding the active ingredient with extenders, e.g. solvents, solid carriers and, where appropriate, surface-active compounds (surfactants).

The compounds of formula I can be mixed with other fungicides, resulting in some cases in unexpected synergistic activities. Mixing components which are particularly preferred are azoles such as azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imazalil, imibenconazole, ipconazole, metconazole, myclobutanil, pefurazoate, penconazole, pyrifenox, prochloraz, propiconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triflumizole or triticonazole; pyrimidinyl carbinoles such as ancymidol,fenarimol or nuacompol; 2-amino-pyrimidine such as bupirimate, dimethirimol or ethirimol; morpholines such as dodemorph, fenpropidin, fenpropimorph, spiroxamin or tridemorph; anilinopyrimidines such as cyprodinil, mepanipyrim or pyrimethanil; pyrroles such as fenpiclonil or fludioxonil; phenylamides such as benalaxyl, furalaxyl, metalaxyl, R-metalaxyl, ofurace or oxadixyl; benzimidazoles such as benomyl, carbendazim, debacarb, fuberidazole or thiabendazole; dicarboximides such as chlozolinate, dichlozoline, iprodione, myclozoline, procymidone or vinclozolin; carboxamides such as carboxin, fenfuram, flutolanil, mepronil, oxycarboxin or thifluzamide; guanidines such as guazatine, dodine or iminoctadine; strobilurines such as azoxystrobin, kresoxim-methyl, metominostrobin, SSF-129, 2-[(2-trifluoromethyl)-pyrid-6-yloxymethyl]-3-methoxyacrylate or 2-[α{[(α-methyl-3-trifluoromethyl-benzyl)imino]-oxy}-o-tolyl]-glyoxylic acid-methylester-O-methyloxime; dithiocarbamates such as ferbam, mancozeb, maneb, metiram, propineb, thiram, zineb or ziram; N-halomethylthiodicarboximides such as captafol, captan, dichlofluanid, fluoromide, folpet or tolyfluanid; copper compounds such as Bordeaux mixture, copper hydroxide, copper oxychloride, copper sulfate, cuprous oxide, mancopper or oxine-copper; nitrophenol derivatives such as dinocap or nitrothal-isopropyl; organo phosphorous derivatives such as edifenphos, iprobenphos, isoprothiolane, phosdiphen, pyrazophos or tolcofos-methyl; and other compounds of diverse structures such as acibenzolar-S-methyl, anilazine, blasticidin-S, chinomethionat, chloroneb, chlorothalonil, cymoxanil, dichlone, diclomezine, dicloran, diethofencarb,dimethomorph, dithianon, etridiazole, famoxadone, fentin, ferimzone, fluazinam, flusulfamide, fenhexamid, fosetyl-aluminium, hymexazol, kasugamycin, methasulfocarb,pencycuron, phthalide, polyoxins, probenazole, propamocarb, pyroquilon, quinoxyfen, quintozene, sulfur, triazoxide, tricyclazole, triforine or validamycin.

The agrochemical compositions usually comprise 0.1 to 99% by weight, preferably 0.1 to 95% by weight, of a compound of formula I, 99.9 to 1% by weight, preferably 99.8 to 5% by weight, of a solid or liquid adjuvant, and 0 to 25% by weight, preferably 0.1 to 25% by weight, of a surfactant.

Whereas commercial products will preferably be formulated as concentrates, the end user will normally employ dilute formulations.

The Examples which follow illustrate the invention described above, without limiting the scope thereof in any way. Temperatures are given in degrees Celsius.

TABLE 1 Compounds of formula I.1 (I.1)

wherein R₁ is methyl and n is the number one and where the combination of R₂, R₃, A and B corresponds to one line in Table A.

TABLE 2 Compounds of formula I.1 wherein R₁ is ethyl and n is the number one and where the combination of R₂, R₃, A and B corresponds to one line in Table A.

TABLE 3 Compounds of formula I.1 wherein R₁ is ethyl and n is zero and where the combination of R₂, R₃, A and B corresponds to one line in Table A.

TABLE 4 Compounds of formula I.1 wherein R₁ is propyl and n is the number one and where the combination of R₂, R₃, A and B corresponds to one line in Table A.

TABLE 5 Compounds of formula I.1 wherein R₁ is propyl and n is zero and where the combination of R₂, R₃, A and B corresponds to one line in Table A.

TABLE 6 Compounds of formula I.1 wherein R₁ is isopropyl and n is the number one and where the combination of R₂, R₃, A and B corresponds to one line in Table A.

TABLE 7 Compounds of formula I.1 wherein R₁ is isopropyl and n is zero and where the combination of R₂, R₃, A and B corresponds to one line in Table A.

TABLE 8 Compounds of formula I.1 wherein R₁ is butyl and n is the number one and where the combination of R₂, R₃, A and B corresponds to one line in Table A.

TABLE 9 Compounds of formula I.1 wherein R₁ is butyl and n is zero and where the combination of R₂, R₃, A and B corresponds to one line in Table A.

TABLE 10 Compounds of formula I.1 wherein R₁ is 3-chloro-propyl and n is the number one and where the combination of R₂, R₃, A and B corresponds to one line in Table A.

TABLE 11 Compounds of formula I.1 wherein R₁ is dimethylamino and n is the number one and where the combination of R₂, R₃, A and B corresponds to one line in Table A.

TABLE 12 Compounds of formula I.1 wherein R₁ is phenyl and n is the number one and where the combination of R₂, R₃, A and B corresponds to one line in Table A.

TABLE 13 Compounds of formula I.1 wherein R₁ is benzyl and n is the number one and where the combination of R₂, R₃, A and B corresponds to one line in Table A.

TABLE 14 Compounds of formula I.2 (I.2)

wherein R₂ is hydrogen and where the combination of R₁, R₃ and n corresponds to one line in Table B.

TABLE 15 Compounds of formula I.3 (I.3)

wherein R₂ is hydrogen and where the combination of R₁, R₃ and n corresponds to one line in Table B.

TABLE 16 Compounds of formula I.4 (I.4)

wherein R₂ is hydrogen and where the combination of R₁, R₃ and n corresponds to one line in Table B.

TABLE 17 Compounds of formula I.5 (I.5)

wherein R₂ is hydrogen and where the combination of R₁, R₃ and n corresponds to one line in Table B.

TABLE 18 Compounds of formula I.6 (I.6)

wherein R₂ is hydrogen and where the combination of R₁, R₃ and n corresponds to one line in Table B.

TABLE 19 Compounds of formula I.7 (I.7)

wherein R₂ is hydrogen and where the combination of R₁, R₃ and n corresponds to one line in Table B.

TABLE 20 Compounds of formula I.8 (I.8)

wherein R₂ is hydrogen and where the combination of R₁, R₃ and n corresponds to one line in Table B.

TABLE 21 Compounds of formula I.9 (I.9)

wherein R₂ is hydrogen and where the combination of R₁, R₃ and n corresponds to one line in Table B.

TABLE 22 Compounds of formula I.10 (I.10)

wherein R₂ is hydrogen and where the combination of R₁, R₃ and n corresponds to one line in Table B.

TABLE 23 Compounds of formula I.11 (I.11)

wherein R₂ is hydrogen and where the combination of R₁, R₃ and n corresponds to one line in Table B.

TABLE 24 Compounds of formula I.12 (I.12)

wherein R₂ is hydrogen and where the combination of R₁, R₃ and n corresponds to one line in Table B.

TABLE 25 Compounds of formula I.13 (I.13)

wherein R₂ is hydrogen and where the combination of R₁, R₃ and n corresponds to one line in Table B.

TABLE 26 Compounds of formula I.14 (I.14)

wherein R₂ is hydrogen and where the combination of R₁, R₃ and n corresponds to one line in Table B.

TABLE 27 Compounds of formula I.15 (I.15)

wherein R₂ is hydrogen and where the combination of R₁, R₃ and n corresponds to one line in Table B.

TABLE 28 Compounds of formula I.16 (I.16)

wherein R₂ is hydrogen and where the combination of R₁, R₃ and n corresponds to one line in Table B

TABLE 29 Compounds of formula I.17 (I.17)

wherein R₂ is hydrogen and where the combination of R₁, R₃ and n corresponds to one line in Table B

TABLE 30 Compounds of formula I.18 (I.18)

wherein R₂ is hydrogen and where the combination of R₁, R₃ and n corresponds to one line in Table B

TABLE 31 Compounds of formula I.19 (I.19)

wherein R₂ is hydrogen and where the combination of R₁, R₃ and n corresponds to one line in Table B

TABLE 32 Compounds of formula I.20 (I.20)

wherein R₂ is hydrogen and where the combination of R₁, R₃ and n corresponds to one line in Table B

TABLE 33 Compounds of formula I.21 (I.21)

wherein R₂ is hydrogen and where the combination of R₁, R₃ and n corresponds to one line in Table B

TABLE 34 Compounds of formula I.22 (I.22)

wherein R₂ is hydrogen and where the combination of R₁, R₃ and n corresponds to one line in Table B

TABLE 35 Compounds of formula I.23 (I.23)

wherein R₂ is hydrogen and where the combination of R₁, R₃ and n corresponds to one line in Table B

TABLE 36 Compounds of formula I.24 (I.24)

wherein R₂ is hydrogen and where the combination of R₁, R₃ and n corresponds to one line in Table B

TABLE 37 Compounds of formula I.25 (I.25)

wherein R₂ is hydrogen and where the combination of R₁, R₃ and n corresponds to one line in Table B

TABLE 38 Compounds of formula I.26 (I.26)

wherein R₂ is hydrogen and where the combination of R₁, R₃ and n corresponds to one line in Table B

TABLE 39 Compounds of formula I.27 (I.27)

wherein R₂ is hydrogen and where the combination of R₁, R₃ and n corresponds to one line in Table B

TABLE 40 Compounds of formula I.28 (I.28)

wherein R₂ is hydrogen and where the combination of R₁, R₃ and n corresponds to one line in Table B

TABLE 41 Compounds of formula I.29 (I.29)

wherein R₂ is hydrogen and where the combination of R₁, R₃ and n corresponds to one line in Table B

TABLE 42 Compounds of formula I.30 (I.30)

wherein R₂ is hydrogen and where the combination of R₁, R₃ and n corresponds to one line in Table B

TABLE 43 Compounds of formula I.31 (I.31)

wherein R₂ is hydrogen and where the combination of R₁, R₃ and n corresponds to one line in Table B

TABLE 44 Compounds of formula I.32 (I.32)

wherein R₂ is hydrogen and where the combination of R₁, R₃ and n corresponds to one line in Table B

TABLE 45 Compounds of formula I.33 (I.33)

wherein R₂ is hydrogen and where the combination of R₁, R₃ and n corresponds to one line in Table B

TABLE 46 Compounds of formula I.34 (I.34)

wherein R₂ is hydrogen and where the combination of R₁, R₃ and n corresponds to one line in Table B

TABLE 47 Compounds of formula I.35 (I.35)

wherein R₂ is hydrogen and where the combination of R₁, R₃ and n corresponds to one line in Table B

TABLE 48 Compounds of formula I.36 (I.36)

wherein R₂ is hydrogen and where the combination of R₁, R₃ and n corresponds to one line in Table B

TABLE 49 Compounds of formula I.37 (I.37)

wherein R₂ is hydrogen and where the combination of R₁, R₃ and n corresponds to one line in Table B

TABLE 50 Compounds of formula I.38 (I.38)

wherein R₂ is hydrogen and where the combination of R₁, R₃ and n corresponds to one line in Table B

TABLE A (wherein Et means ethyl and c. means cyclo) No. R₂ R₃ A B A.1 H phenyl —CH₂— phenyl A.2 H phenyl —CH₂— 4-Cl-phenyl A.3 H phenyl —CH₂— 3,4-di-Cl-phenyl A.4 H phenyl —CH₂— 2,4-di-Cl-phenyl A.5 H phenyl —CH₂— 4-Br-phenyl A.6 H phenyl —CH₂— 4-CH₃-phenyl A.7 H phenyl —CH₂— 4-Et-phenyl A.8 H phenyl —CH₂— 4-OCH₃-phenyl A.9 H phenyl —CH₂— 4-CF₃-phenyl A.10 H phenyl —CH₂— 4-c.C₅H₉-phenyl A.11 H phenyl —CH₂— 3-OCH₃-4-phenoxy-phenyl A.12 H phenyl —CH₂— 3-OCH₃-4-SCH₃-phenyl A.13 H phenyl —CH₂— 4-CH₃OOC-phenyl A.14 H phenyl —CH₂— 3-NO₂-phenyl A.15 H phenyl —CH₂— 4-CN-phenyl A.16 H phenyl —CH₂— 4-N(CH₃)₂-phenyl A.17 H phenyl —CH(CH₃)— phenyl A.18 H phenyl —CH(CH₃)— 4-Cl-phenyl A.19 H phenyl —CH(CH₃)— 3,4-di-Cl-phenyl A.20 H phenyl —CH(CH₃)— 2,4-di-Cl-phenyl A.21 H phenyl —CH(CH₃)— 4-Br-phenyl A.22 H phenyl —CH(CH₃)— 4-CH₃-phenyl A.23 H phenyl —CH(CH₃)— 4-Et-phenyl A.24 H phenyl —CH(CH₃)— 4-OCH₃-phenyl A.25 H phenyl —CH(CH₃)— 4-CF₃-phenyl A.26 H phenyl —CH(CH₃)— 4-c.C₅H₉-phenyl A.27 H phenyl —CH(CH₃)— 3-OCH₃-4-phenoxy-phenyl A.28 H phenyl —CH(CH₃)— 3-OCH₃-4-SCH₃-phenyl A.29 H phenyl —CH(CH₃)— 4-CH₃OOC-phenyl A.30 H phenyl —CH(CH₃)— 3-NO₂-phenyl A.31 H phenyl —CH(CH₃)— 4-CN-phenyl A.32 H phenyl —CH(CH₃)— 4-N(CH₃)₂-phenyl A.33 H phenyl —CH₂CH₂— phenyl A.34 H phenyl —CH₂CH₂— 4-Cl-phenyl A.35 H phenyl —CH₂CH₂— 3,4-di-Cl-phenyl A.36 H phenyl —CH₂CH₂— 2,4-di-Cl-phenyl A.37 H phenyl —CH₂CH₂— 4-Br-phenyl A.38 H phenyl —CH₂CH₂— 4-CH₃-phenyl A.39 H phenyl —CH₂CH₂— 4-Et-phenyl A.40 H phenyl —CH₂CH₂— 4-OCH₃-phenyl A.41 H phenyl —CH₂CH₂— 4-CF₃-phenyl A.42 H phenyl —CH₂CH₂— 4-c.C₅H₉-phenyl A.43 H phenyl —CH₂CH₂— 3-OCH₃-4-phenoxy-phenyl A.44 H phenyl —CH₂CH₂— 3-OCH₃-4-SCH₃-phenyl A.45 H phenyl —CH₂CH₂— 4-CH₃OOC-phenyl A.46 H phenyl —CH₂CH₂— 3-NO₂-phenyl A.47 H phenyl —CH₂CH₂— 4-CN-phenyl A.48 H phenyl —CH₂CH₂— 4-N(CH₃)₂-phenyl A.49 H phenyl —CH(CH₃)CH₂— phenyl A.50 H phenyl —CH(CH₃)CH₂— 4-Cl-phenyl A.51 H phenyl —CH(CH₃)CH₂— 3,4-di-Cl-phenyl A.52 H phenyl —CH(CH₃)CH₂— 2,4-di-Cl-phenyl A.53 H phenyl —CH(CH₃)CH₂— 4-Br-phenyl A.54 H phenyl —CH(CH₃)CH₂— 4-CH₃-phenyl A.55 H phenyl —CH(CH₃)CH₂— 4-Et-phenyl A.56 H phenyl —CH(CH₃)CH₂— 4-OCH₃-phenyl A.57 H phenyl —CH(CH₃)CH₂— 4-CF₃-phenyl A.58 H phenyl —CH(CH₃)CH₂— 4-c.C₅H₉-phenyl A.59 H phenyl —CH(CH₃)CH₂— 3-OCH₃-4-phenoxy-phenyl A.60 H phenyl —CH(CH₃)CH₂— 3-OCH₃-4-SCH₃-phenyl A.61 H phenyl —CH(CH₃)CH₂— 4-CH₃OOC-phenyl A.62 H phenyl —CH(CH₃)CH₂— 3-NO₂-phenyl A.63 H phenyl —CH(CH₃)CH₂— 4-CN-phenyl A.64 H phenyl —CH(CH₃)CH₂— 4-N(CH₃)₂-phenyl A.65 H 4-Cl-phenyl —CH₂— phenyl A.66 H 4-Cl-phenyl —CH₂— 4-Cl-phenyl A.67 H 4-Cl-phenyl —CH₂— 3,4-di-Cl-phenyl A.68 H 4-Cl-phenyl —CH₂— 2,4-di-Cl-phenyl A.69 H 4-Cl-phenyl —CH₂— 4-Br-phenyl A.70 H 4-Cl-phenyl —CH₂— 4-CH₃-phenyl A.71 H 4-Cl-phenyl —CH₂— 4-Et-phenyl A.72 H 4-Cl-phenyl —CH₂— 4-OCH₃-phenyl A.73 H 4-Cl-phenyl —CH₂— 4-CF₃-phenyl A.74 H 4-Cl-phenyl —CH₂— 4-c.C₅H₉-phenyl A.75 H 4-Cl-phenyl —CH₂— 3-OCH₃-4-phenoxy-phenyl A.76 H 4-Cl-phenyl —CH₂— 3-OCH₃-4-SCH₃-phenyl A.77 H 4-Cl-phenyl —CH₂— 4-CH₃OOC-phenyl A.78 H 4-Cl-phenyl —CH₂— 3-NO₂-phenyl A.79 H 4-Cl-phenyl —CH₂— 4-CN-phenyl A.80 H 4-Cl-phenyl —CH₂— 4-N(CH₃)₂-phenyl A.81 H 4-Cl-phenyl —CH(CH₃)— phenyl A.82 H 4-Cl-phenyl —CH(CH₃)— 4-Cl-phenyl A.83 H 4-Cl-phenyl —CH(CH₃)— 3,4-di-Cl-phenyl A.84 H 4-Cl-phenyl —CH(CH₃)— 2,4-di-Cl-phenyl A.85 H 4-Cl-phenyl —CH(CH₃)— 4-Br-phenyl A.86 H 4-Cl-phenyl —CH(CH₃)— 4-CH₃-phenyl A.87 H 4-Cl-phenyl —CH(CH₃)— 4-Et-phenyl A.88 H 4-Cl-phenyl —CH(CH₃)— 4-OCH₃-phenyl A.89 H 4-Cl-phenyl —CH(CH₃)— 4-CF₃-phenyl A.90 H 4-Cl-phenyl —CH(CH₃)— 4-c.C₅H₉-phenyl A.91 H 4-Cl-phenyl —CH(CH₃)— 3-OCH₃-4-phenoxy-phenyl A.92 H 4-Cl-phenyl —CH(CH₃)— 3-OCH₃-4-SCH₃-phenyl A.93 H 4-Cl-phenyl —CH(CH₃)— 4-CH₃OOC-phenyl A.94 H 4-Cl-phenyl —CH(CH₃)— 3-NO₂-phenyl A.95 H 4-Cl-phenyl —CH(CH₃)— 4-CN-phenyl A.96 H 4-Cl-phenyl —CH(CH₃)— 4-N(CH₃)₂-phenyl A.97 H 4-Cl-phenyl —CH₂CH₂— phenyl A.98 H 4-Cl-phenyl —CH₂CH₂— 4-Cl-phenyl A.99 H 4-Cl-phenyl —CH₂CH₂— 3,4-di-Cl-phenyl A.100 H 4-Cl-phenyl —CH₂CH₂— 2,4-di-Cl-phenyl A.101 H 4-Cl-phenyl —CH₂CH₂— 4-Br-phenyl A.102 H 4-Cl-phenyl —CH₂CH₂— 4-CH₃-phenyl A.103 H 4-Cl-phenyl —CH₂CH₂— 4-Et-phenyl A.104 H 4-Cl-phenyl —CH₂CH₂— 4-OCH₃-phenyl A.105 H 4-Cl-phenyl —CH₂CH₂— 4-CF₃-phenyl A.106 H 4-Cl-phenyl —CH₂CH₂— 4-c.C₅H₉-phenyl A.107 H 4-Cl-phenyl —CH₂CH₂— 3-OCH₃-4-phenoxy-phenyl A.108 H 4-Cl-phenyl —CH₂CH₂— 3-OCH₃-4-SCH₃-phenyl A.109 H 4-Cl-phenyl —CH₂CH₂— 4-CH₃OOC-phenyl A.110 H 4-Cl-phenyl —CH₂CH₂— 3-NO₂-phenyl A.111 H 4-Cl-phenyl —CH₂CH₂— 4-CN-phenyl A.112 H 4-Cl-phenyl —CH₂CH₂— 4-N(CH₃)₂-phenyl A.113 H 4-Cl-phenyl —CH(CH₃)CH₂— phenyl A.114 H 4-Cl-phenyl —CH(CH₃)CH₂— 4-Cl-phenyl A.115 H 4-Cl-phenyl —CH(CH₃)CH₂— 3,4-di-Cl-phenyl A.116 H 4-Cl-phenyl —CH(CH₃)CH₂— 2,4-di-Cl-phenyl A.117 H 4-Cl-phenyl —CH(CH₃)CH₂— 4-Br-phenyl A.118 H 4-Cl-phenyl —CH(CH₃)CH₂— 4-CH₃-phenyl A.119 H 4-Cl-phenyl —CH(CH₃)CH₂— 4-Et-phenyl A.120 H 4-Cl-phenyl —CH(CH₃)CH₂— 4-OCH₃-phenyl A.121 H 4-Cl-phenyl —CH(CH₃)CH₂— 4-CF₃-phenyl A.122 H 4-Cl-phenyl —CH(CH₃)CH₂— 4-c.C₅H₉-phenyl A.123 H 4-Cl-phenyl —CH(CH₃)CH₂— 3-OCH₃-4-phenoxy-phenyl A.124 H 4-Cl-phenyl —CH(CH₃)CH₂— 3-OCH₃-4-SCH₃-phenyl A.125 H 4-Cl-phenyl —CH(CH₃)CH₂— 4-CH₃OOC-phenyl A.126 H 4-Cl-phenyl —CH(CH₃)CH₂— 3-NO₂-phenyl A.127 H 4-Cl-phenyl —CH(CH₃)CH₂— 4-CN-phenyl A.128 H 4-Cl-phenyl —CH(CH₃)CH₂— 4-N(CH₃)₂-phenyl A.129 H 3,4-di-Cl-phenyl —CH₂— phenyl A.130 H 3,4-di-Cl-phenyl —CH₂— 4-Cl-phenyl A.131 H 3,4-di-Cl-phenyl —CH₂— 3,4-di-Cl-phenyl A.132 H 3,4-di-Cl-phenyl —CH₂— 2,4-di-Cl-phenyl A.133 H 3,4-di-Cl-phenyl —CH₂— 4-Br-phenyl A.134 H 3,4-di-Cl-phenyl —CH₂— 4-CH₃-phenyl A.135 H 3,4-di-Cl-phenyl —CH₂— 4-Et-phenyl A.136 H 3,4-di-Cl-phenyl —CH₂— 4-OCH₃-phenyl A.137 H 3,4-di-Cl-phenyl —CH₂— 4-CF₃-phenyl A.138 H 3,4-di-Cl-phenyl —CH₂— 4-c.C₅H₉-phenyl A.139 H 3,4-di-Cl-phenyl —CH₂— 3-OCH₃-4-phenoxy-phenyl A.140 H 3,4-di-Cl-phenyl —CH₂— 3-OCH₃-4-SCH₃-phenyl A.141 H 3,4-di-Cl-phenyl —CH₂— 4-CH₃OOC-phenyl A.142 H 3,4-di-Cl-phenyl —CH₂— 3-NO₂-phenyl A.143 H 3,4-di-Cl-phenyl —CH₂— 4-CN-phenyl A.144 H 3,4-di-Cl-phenyl —CH₂— 4-N(CH₃)₂-phenyl A.145 H 3,4-di-Cl-phenyl —CH(CH₃)— phenyl A.146 H 3,4-di-Cl-phenyl —CH(CH₃)— 4-Cl-phenyl A.147 H 3,4-di-Cl-phenyl —CH(CH₃)— 3,4-di-Cl-phenyl A.148 H 3,4-di-Cl-phenyl —CH(CH₃)— 2,4-di-Cl-phenyl A.149 H 3,4-di-Cl-phenyl —CH(CH₃)— 4-Br-phenyl A.150 H 3,4-di-Cl-phenyl —CH(CH₃)— 4-CH₃-phenyl A.151 H 3,4-di-Cl-phenyl —CH(CH₃)— 4-Et-phenyl A.152 H 3,4-di-Cl-phenyl —CH(CH₃)— 4-OCH₃-phenyl A.153 H 3,4-di-Cl-phenyl —CH(CH₃)— 4-CF₃-phenyl A.154 H 3,4-di-Cl-phenyl —CH(CH₃)— 4-c.C₅H₉-phenyl A.155 H 3,4-di-Cl-phenyl —CH(CH₃)— 3-OCH₃-4-phenoxy-phenyl A.156 H 3,4-di-Cl-phenyl —CH(CH₃)— 3-OCH₃-4-SCH₃-phenyl A.157 H 3,4-di-Cl-phenyl —CH(CH₃)— 4-CH₃OOC-phenyl A.158 H 3,4-di-Cl-phenyl —CH(CH₃)— 3-NO₂-phenyl A.159 H 3,4-di-Cl-phenyl —CH(CH₃)— 4-CN-phenyl A.160 H 3,4-di-Cl-phenyl —CH(CH₃)— 4-N(CH₃)₂-phenyl A.161 H 3,4-di-Cl-phenyl —CH₂CH₂— phenyl A.162 H 3,4-di-Cl-phenyl —CH₂CH₂— 4-Cl-phenyl A.163 H 3,4-di-Cl-phenyl —CH₂CH₂— 3,4-di-Cl-phenyl A.164 H 3,4-di-Cl-phenyl —CH₂CH₂— 2,4-di-Cl-phenyl A.165 H 3,4-di-Cl-phenyl —CH₂CH₂— 4-Br-phenyl A.166 H 3,4-di-Cl-phenyl —CH₂CH₂— 4-CH₃-phenyl A.167 H 3,4-di-Cl-phenyl —CH₂CH₂— 4-Et-phenyl A.168 H 3,4-di-Cl-phenyl —CH₂CH₂— 4-OCH₃-phenyl A.169 H 3,4-di-Cl-phenyl —CH₂CH₂— 4-CF₃-phenyl A.170 H 3,4-di-Cl-phenyl —CH₂CH₂— 4-c.C₅C₉-phenyl A.171 H 3,4-di-Cl-phenyl —CH₂CH₂— 3-OCH₃-4-phenoxy-phenyl A.172 H 3,4-di-Cl-phenyl —CH₂CH₂— 3-OCH₃-4-SCH₃-phenyl A.173 H 3,4-di-Cl-phenyl —CH₂CH₂— 4-CH₃OOC-phenyl A.174 H 3,4-di-Cl-phenyl —CH₂CH₂— 3-NO₂-phenyl A.175 H 3,4-di-Cl-phenyl —CH₂CH₂— 4-CN-phenyl A.176 H 3,4-di-Cl-phenyl —CH₂CH₂— 4-N(CH₃)₂-phenyl A.177 H 3,4-di-Cl-phenyl —CH(CH₃)CH₂— phenyl A.178 H 3,4-di-Cl-phenyl —CH(CH₃)CH₂— 4-Cl-phenyl A.179 H 3,4-di-Cl-phenyl —CH(CH₃)CH₂— 3,4-di-Cl-phenyl A.180 H 3,4-di-Cl-phenyl —CH(CH₃)CH₂— 2,4-di-Cl-phenyl A.181 H 3,4-di-Cl-phenyl —CH(CH₃)CH₂— 4-Br-phenyl A.182 H 3,4-di-Cl-phenyl —CH(CH₃)CH₂— 4-CH₃-phenyl A.183 H 3,4-di-Cl-phenyl —CH(CH₃)CH₂— 4-Et-phenyl A.184 H 3,4-di-Cl-phenyl —CH(CH₃)CH₂— 4-OCH₃-phenyl A.185 H 3,4-di-Cl-phenyl —CH(CH₃)CH₂— 4-CF₃-phenyl A.186 H 3,4-di-Cl-phenyl —CH(CH₃)CH₂— 4-c.C₅C₉-phenyl A.187 H 3,4-di-Cl-phenyl —CH(CH₃)CH₂— 3-OCH₃-4-phenoxy-phenyl A.188 H 3,4-di-Cl-phenyl —CH(CH₃)CH₂— 3-OCH₃-4-SCH₃-phenyl A.189 H 3,4-di-Cl-phenyl —CH(CH₃)CH₂— 4-CH₃OOC-phenyl A.190 H 3,4-di-Cl-phenyl —CH(CH₃)CH₂— 3-NO₂-phenyl A.191 H 3,4-di-Cl-phenyl —CH(CH₃)CH₂— 4-CN-phenyl A.192 H 3,4-di-Cl-phenyl —CH(CH₃)CH₂— 4-N(CH₃)₂-phenyl A.193 H 4-Br-phenyl —CH₂CH₂— phenyl A.194 H 4-Br-phenyl —CH₂CH₂— 4-Cl-phenyl A.195 H 4-Br-phenyl —CH₂CH₂— 4-CH₃-phenyl A.196 H 4-Br-phenyl —CH₂CH₂— 4-Et-phenyl A.197 H 4-Br-phenyl —CH₂CH₂— 4-OCH₃-phenyl A.198 H 4-Br-phenyl —CH₂CH₂— 3-OCH₃-4-phenoxy-phenyl A.199 H 4-Br-phenyl —CH₂CH₂— 3-OCH₃-4-SCH₃-phenyl A.200 H 4-Br-phenyl —CH(CH₃)— phenyl A.201 H 4-Br-phenyl —CH(CH₃)— 4-Cl-phenyl A.202 H 4-Br-phenyl —CH(CH₃)— 4-CH₃-phenyl A.203 H 4-Br-phenyl —CH(CH₃)— 4-Et-phenyl A.204 H 4-Br-phenyl —CH(CH₃)— 4-OCH₃-phenyl A.205 H 4-Br-phenyl —CH(CH₃)— 3-OCH₃-4-phenoxy-phenyl A.206 H 4-Br-phenyl —CH(CH₃)— 3-OCH₃-4-SCH₃-phenyl A.207 H 4-CF₃-phenyl —CH₂CH₂— phenyl A.208 H 4-CF₃-phenyl —CH₂CH₂— 4-Cl-phenyl A.209 H 4-CF₃-phenyl —CH₂CH₂— 4-CH₃-phenyl A.210 H 4-CF₃-phenyl —CH₂CH₂— 4-Et-phenyl A.211 H 4-CF₃-phenyl —CH₂CH₂— 4-OCH₃-phenyl A.212 H 4-CF₃-phenyl —CH₂CH₂— 3-OCH₃-4-phenoxy-phenyl A.213 H 4-CF₃-phenyl —CH₂CH₂— 3-OCH₃-4-SCH₃-phenyl A.214 H 4-CF₃-phenyl —CH(CH₃)— phenyl A.215 H 4-CF₃-phenyl —CH(CH₃)— 4-Cl-phenyl A.216 H 4-CF₃-phenyl —CH(CH₃)— 4-CH₃-phenyl A.217 H 4-CF₃-phenyl —CH(CH₃)— 4-Et-phenyl A.218 H 4-CF₃-phenyl —CH(CH₃)— 4-OCH₃-phenyl A.219 H 4-CF₃-phenyl —CH(CH₃)— 3-OCH₃-4-phenoxy-phenyl A.220 H 4-CF₃-phenyl —CH(CH₃)— 3-OCH₃-4-SCH₃-phenyl A.221 H 4-CH₃-phenyl —CH₂CH₂— phenyl A.222 H 4-CH₃-phenyl —CH₂CH₂— 4-Cl-phenyl A.223 H 4-CH₃-phenyl —CH₂CH₂— 4-CH₃-phenyl A.224 H 4-CH₃-phenyl —CH₂CH₂— 4-Et-phenyl A.225 H 4-CH₃-phenyl —CH₂CH₂— 4-OCH₃-phenyl A.226 H 4-CH₃-phenyl —CH₂CH₂— 3-OCH₃-4-phenoxy-phenyl A.227 H 4-CH₃-phenyl —CH₂CH₂— 3-OCH₃-4-SCH₃-phenyl A.228 H 4-CH₃-phenyl —CH(CH₃)— phenyl A.229 H 4-CH₃-phenyl —CH(CH₃)— 4-Cl-phenyl A.230 H 4-CH₃-phenyl —CH(CH₃)— 4-CH₃-phenyl A.231 H 4-CH₃-phenyl —CH(CH₃)— 4-Et-phenyl A.232 H 4-CH₃-phenyl —CH(CH₃)— 4-OCH₃-phenyl A.233 H 4-CH₃-phenyl —CH(CH₃)— 3-OCH₃-4-phenoxy-phenyl A.234 H 4-CH₃-phenyl —CH(CH₃)— 3-OCH₃-4-SCH₃-phenyl A.235 H 4-F-phenyl —CH₂CH₂— 4-Cl-phenyl A.236 H 4-F-phenyl —CH₂CH₂— 4-CH₃-phenyl A.237 H 4-F-phenyl —CH₂CH₂— 4-OCH₃-phenyl A.238 H 4-F-phenyl —CH(CH₃)— 4-Cl-phenyl A.239 H 4-F-phenyl —CH(CH₃)— 4-CH₃-phenyl A.240 H 4-F-phenyl —CH(CH₃)— 4-OCH₃-phenyl A.241 H 4-OCF₃-phenyl —CH₂CH₂— 4-Cl-phenyl A.242 H 4-OCF₃-phenyl —CH₂CH₂— 4-CH₃-phenyl A.243 H 4-OCF₃-phenyl —CH₂CH₂— 4-OCH₃-phenyl A.244 H 4-OCF₃-phenyl —CH(CH₃)— 4-Cl-phenyl A.245 H 4-OCF₃-phenyl —CH(CH₃)— 4-CH₃-phenyl A.246 H 4-OCF₃-phenyl —CH(CH₃)— 4-OCH₃-phenyl A.247 CH₃ 4-Cl-phenyl —CH₂CH₂— 4-Cl-phenyl A.248 CH₃ 4-Cl-phenyl —CH₂CH₂— 4-CH₃-phenyl A.249 CH₃ 4-Cl-phenyl —CH₂CH₂— 4-OCH₃-phenyl A.250 CH₃ 4-Cl-phenyl —CH(CH₃)— 4-Cl-phenyl A.251 CH₃ 4-Cl-phenyl —CH(CH₃)— 4-CH₃-phenyl A.252 CH₃ 4-Cl-phenyl —CH(CH₃)— 4-OCH₃-phenyl A.253 CH₃ 3,4-di-Cl-phenyl —CH₂CH₂— 4-Cl-phenyl A.254 CH₃ 3,4-di-Cl-phenyl —CH₂CH₂— 4-CH₃-phenyl A.255 CH₃ 3,4-di-Cl-phenyl —CH₂CH₂— 4-OCH₃-phenyl A.256 CH₃ 3,4-di-Cl-phenyl —CH(CH₃)— 4-Cl-phenyl A.257 CH₃ 3,4-di-Cl-phenyl —CH(CH₃)— 4-CH₃-phenyl A.258 CH₃ 3,4-di-Cl-phenyl —CH(CH₃)— 4-OCH₃-phenyl A.259 CH₃ 4-Br-phenyl —CH₂CH₂— 4-Cl-phenyl A.260 CH₃ 4-Br-phenyl —CH₂CH₂— 4-CH₃-phenyl A.261 CH₃ 4-Br-phenyl —CH₂CH₂— 4-OCH₃-phenyl A.262 CH₃ 4-Br-phenyl —CH(CH₃)— 4-Cl-phenyl A.263 CH₃ 4-Br-phenyl —CH(CH₃)— 4-CH₃-phenyl A.264 CH₃ 4-Br-phenyl —CH(CH₃)— 4-OCH₃-phenyl A.265 H 3,4-di-OCH₃-phenyl —CH₂CH₂— 4-Cl-phenyl A.266 H 3,4-di-OCH₃-phenyl —CH₂CH₂— 4-CH₃-phenyl A.267 H 3,4-di-OCH₃-phenyl —CH₂CH₂— 4-OCH₃-phenyl A.268 H 3,4-di-OCH₃-phenyl —CH(CH₃)— 4-Cl-phenyl A.269 H 3,4-di-OCH₃-phenyl —CH(CH₃)— 4-CH₃-phenyl A.270 H 3,4-di-OCH₃-phenyl —CH(CH₃)— 4-OCH₃-phenyl A.271 H 3,4-di-CH₃-phenyl —CH₂CH₂— 4-Cl-phenyl A.272 H 3,4-di-CH₃-phenyl —CH₂CH₂— 4-CH₃-phenyl A.273 H 3,4-di-CH₃-phenyl —CH₂CH₂— 4-OCH₃-phenyl A.274 H 3,4-di-CH₃-phenyl —CH(CH₃)— 4-Cl-phenyl A.275 H 3,4-di-CH₃-phenyl —CH(CH₃)— 4-CH₃-phenyl A.276 H 3,4-di-CH₃-phenyl —CH(CH₃)— 4-OCH₃-phenyl A.277 H 4-Cl-phenyl —CH₂CH₂— 3-OCH₃-phenyl A.278 H 4-Cl-phenyl —(CH₂)₃— 3,4-di-CH₃O-phenyl

TABLE B (wherein Et means ethyl) No. R₁ n R₃ B.1 CH₃ 1 4-Cl-phenyl B.2 Et 0 4-Cl-phenyl B.3 Et 1 4-Cl-phenyl B.4 1-propyl 0 4-Cl-phenyl B.5 1-propyl 1 4-Cl-phenyl B.6 2-propyl 0 4-Cl-phenyl B.7 2-propyl 1 4-Cl-phenyl B.8 1-butyl 0 4-Cl-phenyl B.9 1-butyl 1 4-Cl-phenyl B.10 N(CH₃)₂ 0 4-Cl-phenyl B.11 N(CH₃)₂ 1 4-Cl-phenyl B.12 1-pyrrolidin 1 4-Cl-phenyl B.13 3-Cl-propyl 1 4-Cl-phenyl B.14 2-Me-2-propyl 0 4-Cl-phenyl B.15 2-Me-propyl 1 4-Cl-phenyl B.16 CF₃ 1 4-Cl-phenyl B.17 CH₂—CF₃ 1 4-Cl-phenyl B.18 vinyl 1 4-Cl-phenyl B.19 cyclopentyl 0 4-Cl-phenyl B.20 cyclohexyl 0 4-Cl-phenyl B.21 cyclopentyl 1 4-Cl-phenyl B.22 cyclohexyl 1 4-Cl-phenyl B.23 CH₂—SO₂—CH₃ 1 4-Cl-phenyl B.24 phenyl 1 4-Cl-phenyl B.25 benzyl 1 4-Cl-phenyl B.26 4-Me-phenyl 1 4-Cl-phenyl B.27 4-MeS-phenyl 1 4-Cl-phenyl B.28 4-CF₃-phenyl 1 4-Cl-phenyl B.29 4-CF₃O-phenyl 1 4-Cl-phenyl B.30 4-MeO-phenyl 1 4-Cl-phenyl B.31 3-CH₃OOC-phenyl 1 4-Cl-phenyl B.32 3-CH₃CO-phenyl 1 4-Cl-phenyl B.33 4-Cl-phenyl 1 4-Cl-phenyl B.34 3-NO₂-phenyl 1 4-Cl-phenyl B.35 3-CN-phenyl 1 4-Cl-phenyl B.36 CH₃ 1 3,4-di-Cl-phenyl B.37 Et 0 3,4-di-Cl-phenyl B.38 Et 1 3,4-di-Cl-phenyl B.39 1-propyl 0 3,4-di-Cl-phenyl B.40 1-propyl 1 3,4-di-Cl-phenyl B.41 2-propyl 0 3,4-di-Cl-phenyl B.42 2-propyl 1 3,4-di-Cl-phenyl B.43 1-butyl 0 3,4-di-Cl-phenyl B.44 1-butyl 1 3,4-di-Cl-phenyl B.45 N(CH₃)₂ 0 3,4-di-Cl-phenyl B.46 N(CH₃)₂ 1 3,4-di-Cl-phenyl B.47 1-pyrrolidin 1 3,4-di-Cl-phenyl B.48 3-Cl-propyl 1 3,4-di-Cl-phenyl B.49 2-Me-2-propyl 0 3,4-di-Cl-phenyl B.50 2-Me-propyl 1 3,4-di-Cl-phenyl B.51 CF₃ 1 3,4-di-Cl-phenyl B.52 CH₂—CF₃ 1 3,4-di-Cl-phenyl B.53 vinyl 1 3,4-di-Cl-phenyl B.54 cyclopentyl 0 3,4-di-Cl-phenyl B.55 cyclohexyl 0 3,4-di-Cl-phenyl B.56 cyclopentyl 1 3,4-di-Cl-phenyl B.57 cyclohexyl 1 3,4-di-Cl-phenyl B.58 CH₂—SO₂—CH₃ 1 3,4-di-Ci-phenyl B.59 phenyl 1 3,4-di-Cl-phenyl B.60 benzyl 1 3,4-di-Cl-phenyl B.61 4-Me-phenyl 1 3,4-di-Cl-phenyl B.62 4-MeS-phenyl 1 3,4-di-Cl-phenyl B.63 4-CF₃-phenyl 1 3,4-di-Cl-phenyl B.64 4-CF₃O-phenyl 1 3,4-di-Cl-phenyl B.65 4-MeO-phenyl 1 3,4-di-Cl-phenyl B.66 3-CH₃OOC-phenyl 1 3,4-di-Cl-phenyl B.67 3-CH₃CO-phenyl 1 3,4-di-Cl-phenyl B.68 4-Cl-phenyl 1 3,4-di-Cl-phenyl B.69 3-NO₂-phenyl 1 3,4-di-Cl-phenyl B.70 3-CN-phenyl 1 3,4-di-Cl-phenyl B.71 CH₃ 1 phenyl B.72 Et 0 phenyl B.73 Et 1 phenyl B.74 2-propyl 0 phenyl B.75 2-propyl 1 phenyl B.76 N(CH₃)₂ 1 phenyl B.77 CH₃ 1 4-Br-phenyl B.78 Et 0 4-Br-phenyl B.79 Et 1 4-Br-phenyl B.80 2-propyl 0 4-Br-phenyl B.81 2-propyl 1 4-Br-phenyl B.82 N(CH₃)₂ 1 4-Br-phenyl B.83 CH₃ 1 4-CH₃-phenyl B.84 Et 0 4-CH₃-phenyl B.85 Et 1 4-CH₃-phenyl B.86 2-propyl 0 4-CH₃-phenyl B.87 2-propyl 1 4-CH₃-phenyl B.88 N(CH₃)₂ 1 4-CH₃-phenyl B.89 CH₃ 1 4-CH₃O-phenyl B.90 Et 0 4-CH₃O-phenyl B.91 Et 1 4-CH₃O-phenyl B.92 2-propyl 0 4-CH₃O-phenyl B.93 2-propyl 1 4-CH₃O-phenyl B.94 N(CH₃)₂ 1 4-CH₃O-phenyl B.95 CH₃ 1 4-CF₃-phenyl B.96 Et 0 4-CF₃-phenyl B.97 Et 1 4-CF₃-phenyl B.98 2-propyl 0 4-CF₃-phenyl B.99 2-propyl 1 4-CF₃-phenyl B.100 N(CH₃)₂ 1 4-CF₃-phenyl B.101 CH₃ 1 4-F-phenyl B.102 Et 0 4-F-phenyl B.103 Et 1 4-F-phenyl B.104 2-propyl 0 4-F-phenyl B.105 2-propyI 1 4-F-phenyl B.106 N(CH₃)₂ 1 4-F-phenyl B.107 CH₃ 1 4-CF₃O-phenyl B.108 Et 0 4-CF₃O-phenyl B.109 Et 1 4-CF₃O-phenyl B.110 2-propyl 0 4-CF₃O-phenyl B.111 2-propyl 1 4-CF₃O-phenyl B.112 N(CH₃)₂ 1 4-CF₃O-phenyl B.113 CH₃ 1 3,4-di-CH₃-phenyl B.114 Et 0 3,4-di-CH₃-phenyl B.115 Et 1 3,4-di-CH₃-phenyl B.116 2-propyl 0 3,4-di-CH₃-phenyl B.117 2-propyl 1 3,4-di-CH₃-phenyl B.118 N(CH₃)₂ 1 3.4-di-CH₃-phenyl B.119 CH₃ 1 4-vinyl-phenyl B.120 Et 0 4-vinyl-phenyl B.121 Et 1 4-vinyl-phenyl B.122 2-propyl 0 4-vinyl-phenyl B.123 2-propyl 1 4-vinyl-phenyl B.124 N(CH₃)₂ 1 4-vinyl-phenyl B.125 CH₃ 1 4-ethynyl-phenyl B.126 Et 0 4-ethynyl-phenyl B.127 Et 1 4-ethynyl-phenyl B.128 2-propyl 0 4-ethynyl-phenyl B.129 2-propyl 1 4-ethynyl-phenyl B.130 N(CH₃)₂ 1 4-ethynyl-phenyl B.131 CH₃ 1 4-cyclopentyl-phenyl B.132 Et 0 4-cyclopentyl-phenyl B.133 Et 1 4-cyclopentyl-phenyl B.134 2-propyl 0 4-cyclopentyl-phenyl B.135 2-propyl 1 4-cyclopentyl-phenyl B.136 N(CH₃)₂ 1 4-cyclopentyl-phenyl B.137 Et 0 4-allylO-phenyl B.138 Et 1 4-allylO-phenyl B.139 2-propyl 0 4-allylO-phenyl B.140 2-propyl 1 4-allylO-phenyl B.141 N(CH₃)₂ 1 4-allylO-phenyl B.142 Et 0 4-CH₃S-phenyl B.143 Et 1 4-CH₃S-phenyl B.144 2-propyl 0 4-CH₃S-phenyl B.145 2-propyl 1 4-CH₃S-phenyl B.146 N(CH₃)₂ 1 4-CH₃S-phenyl B.147 Et 0 4-CH₃-SO₂-phenyl B.148 Et 1 4-CH₃-SO₂-phenyl B.149 2-propyl 0 4-CH₃-SO₂-phenyl B.150 2-propyl 1 4-CH₃-SO₂-phenyl B.151 N(CH₃)₂ 1 4-CH₃-SO₂-phenyl B.152 Et 0 3-CH₃CO-phenyl B.153 Et 1 3-CH₃CO-phenyl B.154 2-propyl 0 3-CH₃CO-phenyl B.155 2-propyl 1 3-CH₃CO-phenyl B.156 N(CH₃)₂ 1 3-CH₃CO-phenyl B.157 Et 0 3-CH₃OOC-phenyl B.158 Et 1 3-CH₃OOC-phenyl B.159 2-propyl 0 3-CH₃OOC-phenyl B.160 2-propyl 1 3-CH₃OOC-phenyl B.161 N(CH₃)₂ 1 3-CH₃OOC-phenyl B.162 Et 0 4-N(CH₃)₂-phenyl B.163 Et 1 4-N(CH₃)₂-phenyl B.164 2-propyl 0 4-N(CH₃)₂-phenyl B.165 2-propyl 1 4-N(CH₃)₂-phenyl B.166 N(CH₃)₂ 1 4-N(CH₃)₂-phenyl B.167 Et 0 3-NO₂-phenyl B.168 Et 1 3-NO₂-phenyl B.169 2-propyl 0 3-NO₂-phenyl B.170 2-propyl 1 3-NO₂-phenyl B.171 N(CH₃)₂ 1 3-NO₂-phenyl B.172 Et 0 4-CN-phenyl B.173 Et 1 4-CN-phenyl B.174 2-propyl 0 4-CN-phenyl B.175 2-propyl 1 4-CN-phenyl B.176 N(CH₃)₂ 1 4-CN-phenyl B.177 Et 0 4-OH-phenyl B.178 Et 1 4-OH-phenyl B.179 2-propyl 0 4-OH-phenyl B.180 2-propyl 1 4-OH-phenyl B.181 N(CH₃)₂ 1 4-OH-phenyl B.182 Et 0 2-thienyl B.183 Et 1 2-thienyl B.184 2-propyl 0 2-thienyl B.185 2-propyl 1 2-thienyl B.186 N(CH₃)₂ 1 2-thienyl B.187 Et 0 3-thienyl B.188 Et 1 3-thienyl B.189 2-propyl 0 3-thienyl B.190 2-propyl 1 3-thienyl B.191 N(CH₃)₂ 1 3-thienyl B.192 Et 0 2-furanyl B.193 Et 1 2-furanyl B.194 2-propyl 0 2-furanyl B.195 2-propyl 1 2-furanyl B.196 N(CH₃)₂ 1 2-furanyl B.197 Et 0 1-naphthyl B.198 Et 1 1-naphthyl B.199 2-propyl 0 1-naphthyl B.200 2-propyl 1 1-naphthyl B.201 N(CH₃)₂ 1 1-naphthyl B.202 Et 0 2-naphthyl B.203 Et 1 2-naphthyl B.204 2-propyl 0 2-naphthyl B.205 2-propyl 1 2-naphthyl B.206 N(CH₃)₂ 1 2-naphthyl B.207 Et 0 3-pyridyl B.208 Et 1 3-pyridyl B.209 2-propyl 0 3-pyridyl B.210 2-propyl 1 3-pyridyl B.211 N(CH₃)₂ 1 3-pyridyl B.212 Et 0 2-benzothiazolyl B.213 Et 1 2-benzothiazolyl B.214 2-propyl 0 2-benzothiazolyl B.215 2-propyl 1 2-benzothiazolyl B.216 N(CH₃)₂ 1 2-benzothiazolyl B.217 Et 0 3-indolyl B.218 Et 1 3-indolyl B.219 2-propyl 0 3-indolyl B.220 2-propyl 1 3-indolyl B.221 N(CH₃)₂ 1 3-indolyl B.222 Et 0 3-CF₃-phenyl B.223 Et 1 3-CF₃-phenyl B.224 2-propyl 0 3-CF₃-phenyl B.225 2-propyl 1 3-CF₃-phenyl B.226 N(CH₃)₂ 1 3-CF₃-phenyl B.227 Et 0 4-phenoxy-phenyl B.228 Et 1 4-phenoxy-phenyl B.229 2-propyl 0 4-phenoxy-phenyl B.230 2-propyl 1 4-phenoxy-phenyl B.231 N(CH₃)₂ 1 4-phenoxy-phenyl B.232 Et 0 4-ethoxy-phenyl B.233 Et 1 4-ethoxy-phenyl B.234 2-propyl 0 4-ethoxy-phenyl B.235 2-propyl 1 4-ethoxy-phenyl B.236 N(CH₃)₂ 1 4-ethoxy-phenyl B.237 Et 0 3,4-O—CH₂—O-phenyl B.238 Et 1 3,4-O—CH₂—O-phenyl B.239 2-propyl 0 3,4-O—CH₂—O-phenyl B.240 2-propyl 1 3,4-O—CH₂—O-phenyl B.241 N(CH₃)₂ 1 3,4-O—CH₂—O-phenyl B.242 Et 0 3,4-O—CH₂CH₂—O-phenyl B.243 Et 1 3,4-O—CH₂CH₂—O-phenyl B.244 2-propyl 0 3,4-O—CH₂CH₂—O-phenyl B.245 2-propyl 1 3,4-O—CH₂CH₂—O-phenyl B.246 N(CH₃)₂ 1 3,4-O—CH₂CH₂—O-phenyl B.247 Et 0 4-biphenyl B.248 Et 1 4-biphenyl B.249 2-propyl 0 4-biphenyl B.250 2-propyl 1 4-biphenyl B.251 N(CH₃)₂ 1 4-biphenyl B.252 Et 0 4-isopropyl-phenyl B.253 Et 1 4-isopropyl-phenyl B.254 2-propyl 0 4-isopropyl-phenyl B.255 2-propyl 1 4-isopropyl-phenyl B.256 N(CH₃)₂ 1 4-isopropyl-phenyl B.257 Et 0 4-CH₃OOC-phenyl B.258 Et 1 4-CH₃OOC-phenyl B.259 2-propyl 0 4-CH₃OOC-phenyl B.260 2-propyl 1 4-CH₃OOC-phenyl B.261 N(CH₃)₂ 1 4-CH₃OOC-phenyl B.262 Et 0 3,4-di-F-phenyl B.263 Et 1 3,4-di-F-phenyl B.264 2-propyl 0 3,4-di-F-phenyl B.265 2-propyl 1 3,4-di-F-phenyl B.266 N(CH₃)₂ 1 3,4-di-F-phenyl B.267 Et 0 4-tert.butyl-phenyl B.268 Et 1 4-tert.butyl-phenyl B.269 2-propyl 0 4-tert.butyl-phenyl B.270 2-propyl 1 4-tert.butyl-phenyl B.271 N(CH₃)₂ 1 4-tert.butyl-phenyl B.272 Et 0 3-Cl-phenyl B.273 Et 1 3-Cl-phenyl B.274 2-propyl 0 3-Cl-phenyl B.275 2-propyl 1 3-Cl-phenyl B.276 N(CH₃)₂ 1 3-Cl-phenyl B.277 Et 0 3,5-di-Cl-phenyl B.278 Et 1 3,5-di-Cl-phenyl B.279 2-propyl 0 3,5-di-Cl-phenyl B.280 2-propyl 1 3,5-di-Cl-phenyl B.281 N(CH₃)₂ 1 3,5-di-Cl-phenyl B.282 Et 0 3-pyrazolyl B.283 Et 1 3-pyrazolyl B.284 2-propyl 0 3-pyrazolyl B.285 2-propyl 1 3-pyrazolyl B.286 N(CH₃)₂ 1 3-pyrazolyl B.287 Et 0 1-Me-2-benzimidazolyl B.288 Et 1 1-Me-2-benzimidazoiyl B.289 2-propyl 0 1-Me-2-benzimidazolyl B.290 2-propyl 1 1-Me-2-benzimidazolyl B.291 N(CH₃)₂ 1 1-Me-2-benzimidazolyl B.292 Et 0 2-thiazolyl B.293 Et 1 2-thiazolyl B.294 2-propyl 0 2-thiazolyl B.295 2-propyl 1 2-thiazolyl B.296 N(CH₃)₂ 1 2-thiazolyl B.297 Et 0 1-Me-3-indolyl B.298 Et 1 1-Me-3-indolyl B.299 2-propyl 0 1-Me-3-indolyl B.300 2-propyl 1 1-Me-3-indolyl B.301 N(CH₃)₂ 1 1-Me-3-indolyl B.302 Et 0 2-pyrrolyl B.303 Et 1 2-pyrrolyl B.304 2-propyl 0 2-pyrrolyl B.305 2-propyl 1 2-pyrrolyl B.306 N(CH₃)₂ 1 2-pyrrolyl B.307 Et 0 2-imidazolyl B.308 Et 1 2-imidazolyl B.309 2-propyl 0 2-imidazolyl B.310 2-propyl 1 2-imidazolyl B.311 N(CH₃)₂ 1 2-imidazolyl B.312 Et 0 4-imidazolyl B.313 Et 1 4-imidazolyl B.314 2-propyl 0 4-imidazolyl B.315 2-propyl 1 4-imidazolyl B.316 N(CH₃)₂ 1 4-imidazolyl B.317 1-propyl 1 4-CF₃O-phenyl B.318 Et 1 3,4-di-CH₃O-phenyl B.319 1-propyl 1 4-Br-phenyl B.320 N(CH₃)₂ 1 3,4-di-CH₃O-phenyl B.321 1-propyl 1 3,4-di-CH₃O-phenyl B.322 1-propyl 1 4-N(CH₃)₂-phenyl B.323 1-propyl 1 4-CH₃S-phenyl B.324 Et 1 3-CH₃-phenyl B.325 N(CH₃)₂ 1 3-CH₃-phenyl B.326 1-propyl 1 3-CH₃-phenyl B.327 1-propyl 1 4-CH₃-phenyl B.328 N(CH₃)₂ 1 3-CF₃-phenyl B.329 1-propyl 1 3-CF₃-phenyl B.330 1-propyl 1 4-phenoxy-phenyl B.331 1-propyl 1 4-ethoxy-phenyl B.332 1-propyl 1 3,4-O-CH₂-O-phenyl B.333 CH₃ 1 3-F,4-Cl-phenyl B.334 Et 1 3-F,4-Cl-phenyl B.335 N(CH₃)₂ 1 3-F,4-Cl-phenyl B.336 N(CH₃)₂ 1 3-CF₃,4-Cl-phenyl B.337 Et 1 3-CF₃,4-Cl-phenyl B.338 CH₃ 1 3-CF₃,4-Cl-phenyl B.339 Et 1 3-F-phenyl B.340 Et 1 5-Me,2-thienyl B.341 1-propyl 1 2-naphthyl B.342 n-butyl 1 4-Br-phenyl B.343 vinyl 1 4-Br-phenyl B.344 4-Me-phenyl 1 4-Br-phenyl B.345 Et 1 2-CH₃O-phenyl B.346 Et 1 3-CH₃O-phenyl B.347 Et 1 2-Cl-phenyl B.348 Et 1 3,5-di-F-phenyl B.349 Et 1 3-CH₃,4-CH₃O-phenyl B.350 Et 1 4-NHCOCH₃-phenyl B.351 Et 1 3,5-di-CH₃O-phenyl B.352 Et 1 4-pyrrolidino-phenyl B.353 Et 1 3-Br-phenyl B.354 Et 1 3-CH₃O,4-propargyloxy-phenyl B.355 Et 1 4-Br,2-thienyl B.356 Et 1 2-fluorenyl B.357 Et 1 4-CH(O-Et)₂-phenyl B.358 Et 1 4-(4′-Cl-phenoxy)-phenyl B.359 Et 1 5-Me,2-furanyl B.360 Et 1 3-Cl-phenyl B.361 Et 1 4-NO₂-phenyl B.362 Et 1 2,4-di-CH₃O-phenyl B.363 Et 1 2,4-di-Cl-phenyl B.364 N(CH₃)₂ 1 5-Me,2-furanyl B.365 N(CH₃)₂ 1 3-F-phenyl B.366 N(CH₃)₂ 1 5-Me,2-thienyl B.367 N(CH₃)₂ 1 2-CH₃O-phenyl B.368 N(CH₃)₂ 1 3-CH₃O-phenyl B.369 N(CH₃)₂ 1 2-Cl-phenyl B.370 N(CH₃)₂ 1 3,5-di-F-phenyl B.371 N(CH₃)₂ 1 3-CH₃,4-CH₃O-phenyl B.372 N(CH₃)₂ 1 4-NO₂-phenyl B.373 N(CH₃)₂ 1 3,5-di-CH₃O-phenyl B.374 N(CH₃)₂ 1 2,4-di-CH₃O-phenyl B.375 N(CH₃)₂ 1 2,4-di-Cl-phenyl B.376 N(CH₃)₂ 1 4-pyrrolidino-phenyl B.377 N(CH₃)₂ 1 3-Br-phenyl B.378 N(CH₃)₂ 1 3-CH₃O,4-propargyloxy-phenyl B.379 N(CH₃)₂ 1 4-Br,2-thienyl B.380 N(CH₃)₂ 1 4-(4′-Cl-phenoxy)-phenyl B.381 N(CH₃)₂ 1 2-fluorenyl

Preparation Examples for the Compounds of Formula I EXAMPLE 1 2-(4-Chloro-phenyl)-N-[2-(3,4-dimethoxy-phenyl)-ethyl]-2-ethanesulfonylamino-acetamide

To a vigorously stirred solution of 8 g amino-(4-chloro-phenyl)-acetic acid (J.Chem.Soc.,1962,1440) and 1.7 g sodium hydroxide in 125 ml water at 0° C. is added simultaneously a solution of 5.6 g ethanesulfonyl chloride in 100 ml toluene and a solution of 1.7 g sodium hydroxide in 100 ml water during 20 minutes. The reaction mixture is stirred for 45 min at 0° C. Stirring is continued for 3 hours during which the reaction mixture is allowed to warm to room temperature.

The organic phase is separated and extracted with 100 ml 2N sodium hydroxide solution. The water phases are combined and acidified with conc. hydrochloric acid to pH<2 and extracted with ethyl acetate (2×500 ml). The organic phases are washed with brine solution (2×150 ml), dried over magnesium sulfate and evaporated to dryness, yielding (4-chloro-phenyl)-ethanesulfonamino-acetic acid as yellow oil.

To a solution of 2.5 g (4-chloro-phenyl)-ethanesulfonamino-acetic acid, 1.6 g homoveratrylamine and 3.1 ml N,N-diisopropylethylamine in 40 ml N,N-dimethylformamide is added 4 g benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate. The reaction mixture is stirred for 2 hours at room temperature. 500 ml water is added and extracted twice with ethyl acetate (2×300 ml). The organic phases are washed with brine (2×100 ml), combined, died over magnesium sulfate and evaporated to dryness. The residue is purified by flash column chromatography on silica get using ethyl acetate/hexane 2:1 as eluent. 2-(4-chloro-phenyl)-N-[2-(3,4-dimethoxy-phenyl)-ethyl]-2-ethanesulfonylamino-acetamide is obtained (cmpd. Tab.14,B.3) and recrystallized from ethyl acetate/hexane, m.p. 136-138° C.

EXAMPLE 2 2-Benzo[1,3]dioxol-5-yl-N-[2-(3,4-dimethoxy-phenyl)-ethyl]-2-(N′,N′-dimethylsulfamido)-acetamide

A mixture of 4.78 g (25.0 mmol) 4-(2-isocyano-ethyl)-1,2-dimethoxy-benzene, 4.5 g (30 mmol) piperonal, 3.15 g (50 mmol) ammonium formiate in 25 ml methanol (which has been previously purged by a nitrogen stream) is heated at reflux for 18 hours. The solution is cooled to 0° C. and 10 ml HCl 10M in methanol is added. The reaction mixture is stirred at RT for 10 hours. The mixture is then extracted with 2 fold 150 ml ice-cooled water. The water phase is made basic by the addition of NaOH 2N (pH=14) and is extracted with ethyl acetate. 7.33 g (82%) 2-amino-2-benzo[1,3]dioxol-5-yl-N-[2-(3,4-dimethoxy-phenyl)-ethyl]acetamide is isolated as an orange oil which is further reacted without purification. 1.9 g (5.3 mmol) 2-amino-2-benzo[1,3]dioxol-5-yl-N-[2-(3,4-dimethoxy-phenyl)-ethyl]-acetamide is dissolved in 20 ml THF and cooled to 0° C. 0.8 ml (7.42 mmol) N,N-dimethyl-sulfamoyl chloride and 2.22 ml (15.9 mmol) triethylamine are added and the mixture is stirred 15 hours at RT. After dilution with ethyl acetate, the mixture is extracted with ice-cooled water. Evaporation of the solvent give an oil which is crystallized in toluene to give 1.08 g (44%) 2-benzo[1,3]dioxol-5-yl-N-[2-(3,4-dimethoxy-phenyl)-ethyl]-2-(N′,N′-dimethylsulfamido)-acetamide (cmpd. Tab.14,B.241) as a white solid (m.p. 137.5-139° C.). From the mother liquor 0.85 g (35%) compound is further isolated.

The compounds given in Table C can be obtained analogously to Examples 1 or 2.

TABLE C physical data Compound Stereochemistry m.p. or M(ESMS) Tab.2, A.277 R, S 113-115 Tab.2, A.278 R, S 123-124° C. Tab.14, B.3 R, S 136-138° C. Tab.14, B.38 R, S 473(M − 1)− Tab.14, B.38 R 126-127° C. Tab.14, B.46 R oil Tab.14, B.73 R, S 157-159° C. Tab.14, B.77 R, S 167-168.5° C. Tab.14, B.79 R, S 143-145° C. Tab.14, B.81 R, S 497(M − 1)− Tab.14, B.82 R, S 114-116° C. Tab.14, B.85 R, S 135-136° C. Tab.14, B.88 R, S 118.5-119.5° C. Tab.14, B.91 R, S 116-127° C.; 437(M + 1)+ Tab.14, B.94 R, S 452(M + 1)+ Tab.14, B.97 R, S 150-153° C. Tab.14, B.103 R, S 161-163° C. Tab.14, B.109 R, S 154-155° C. Tab.14, B.112 R, S 506(M + 1)+ Tab.14, B.143 R, S 155.5-156.5° C. Tab.14, B.146 R, S 102.5-104.5° C. Tab.14, B.163 R, S 146-148° C. Tab.14, B.166 R, S 109-110° C. Tab.14, B.173 R, S 145-147° C. Tab.14, B.176 R, S 445(M − 1)− Tab.14, B.183 R, S 136-137.5° C. Tab.14, B.186 R, S 426(M − 1)− Tab.14, B.193 R, S 395(M − 1)− Tab.14, B.196 R, S 410(M − 1)− Tab.14, B.198 R, S 144-146° C. Tab.14, B.201 R, S 470(M − 1)− Tab.14, B.203 R, S 135-136.5° C. Tab.14, B.206 R, S 472(M + 1)+ Tab.14, B.223 R, S 103-107° C. Tab.14, B.228 R, S 134-136° C. Tab.14, B.231 R, S 128.5-131° C. Tab.14, B.233 R, S 137.5-138.5° C. Tab.14, B.236 R, S 119-121 Tab.14, B.238 R, S 188-189.5° C. Tab.14, B.241 R, S 137.5-139° C. Tab.14, B.248 R, S 144-144.5° C.; 483(M + 1)+ Tab.14, B.251 R, S 125-126.5° C.; 498(M + 1)+ Tab.14, B.253 R, S 163-164° C. Tab.14, B.256 R, S 464(M + 1)+ Tab.14, B.258 R, S 140-141.5° C.; 465(M + 1)+ Tab.14, B.261 R, S 126-127° C.; 480(M + 1)+ Tab.14, B.263 R, S 149.5-151° C. Tab.14, B.266 R, S 458(M + 1)+ Tab.14, B.268 R, S 174-176° C. Tab.14, B.271 R, S 476(M − 1)− Tab.14, B.273 R, S 123-125° C. Tab.14, B.276 R, S 117-118° C.; 456(M + 1)+ Tab.14, B.278 R, S 120.5-122° C. Tab.14, B.281 R, S 155-157° C. Tab.14, B.317 R, S 115.5-118.5° C. Tab.14, B.318 R, S 159.5-160.5° C. Tab.14, B.319 R, S 136-137° C. Tab.14, B.320 R, S 142-143° C. Tab.14, B.321 R, S 139-141° C. Tab.14, B.322 R, S 125.5-126.5° C. Tab.14, B.323 R, S 130.5-135.5° C. Tab.14, B.324 R, S 112.5-113.5° C. Tab.14, B.325 R, S 434(M − 1)− Tab.14, B.326 R, S 433(M − 1)− Tab.14, B.327 R, S 116-117° C. Tab.14, B.328 R, S 488(M − 1)− Tab.14, B.329 R, S 487(M − 1)− Tab.14, B.330 R, S 83-85° C. Tab.14, B.331 R, S 132.5-134° C. Tab.14, B.332 R, S 134-136° C. Tab.14, B.333 R, S 141-142° C. Tab.14, B.334 R, S 139-141° C. Tab.14, B.335 R, S 122-123° C. Tab.14, B.336 R, S oil Tab.14, B.337 R, S 115-117° C. Tab.14, B.338 R, S 108-110° C. Tab.14, B.339 R, S 425(M + 1)+ Tab.14, B.340 R, S 427(M + 1)+ Tab.14, B.341 R, S 471(M + 1)+ Tab.14, B.342 R, S 127.5-129.5° C. Tab.14, B.343 R, S 152.5-154.5° C. Tab.14, B.344 R, S 166-167° C. Tab.14, B.345 R, S 437(M + 1)+ Tab.14, B.346 R, S 437(M + 1)+ Tab.14, B.347 R, S 441(M + 1)+ Tab.14, B.348 R, S 443(M + 1)+ Tab.14, B.349 R, S 451(M + 1)+ Tab.14, B.351 R, S 467(M + 1)+ Tab.14, B.352 R, S 476(M + 1)+ Tab.14, B.353 R, S 486(M + 1)+ Tab.14, B.354 R, S 491(M + 1)+ Tab.14, B.355 R, S 492(M + 1)+ Tab.14, B.359 R, S 411(M + 1)+ Tab.14, B.360 R, S 441(M + 1)+ Tab.14, B.361 R, S 452(M + 1)+ Tab.14, B.362 R, S 467(M + 1)+ Tab.14, B.363 R, S 476(M + 1)+ Tab.14, B.364 R, S 426(M + 1)+ Tab.14, B.365 R, S 440(M + 1)+ Tab.14, B.366 R, S 442(M + 1)+ Tab.14, B.367 R, S 452(M + 1)+ Tab.14, B.368 R, S 452(M + 1)+ Tab.14, B.369 R, S 456(M + 1)+ Tab.14, B.370 R, S 459(M + 1)+ Tab.14, B.371 R, S 466(M + 1)+ Tab.14, B.372 R, S 467(M + 1)+ Tab.14, B.373 R, S 482(M + 1)+ Tab.14, B.374 R, S 482(M + 1)+ Tab.14, B.375 R, S 491(M + 1)+ Tab.14, B.378 R, S 506(M + 1)+ Tab.14, B.379 R, S 507(M + 1)+ Tab.14, B.380 R, S 549(M + 1)+ Tab.15, B.3 R, S 147-148° C. Tab.15, B.73 R, S 121-122° C. Tab.15, B.85 R, S 147-150° C. Tab.15, B.91 R, S 156-158° C. Tab.15, B.97 R, S 160-165° C. Tab.15, B.103 R, S 141-143° C. Tab.16, B.3 R, S 140-145° C. Tab.16, B.91 R, S 463(M + 1)+ Tab.16, B.193 R, S 437(M + 1)+ Tab.16, B.248 R, S 509(M + 1)+ Tab.16, B.258 R, S 491(M + 1)+ Tab.16, B.273 R, S 467(M + 1)+ Tab.16, B.278 R, S 502(M + 1)+ Tab.16, B.334 R, S 158-159° C. Tab.16, B.339 R, S 451(M + 1)+ Tab.16, B.340 R, S 453(M + 1)+ Tab.16, B.345 R, S 463(M + 1)+ Tab.16, B.346 R, S 463(M + 1)+ Tab.16, B.347 R, S 467(M + 1)+ Tab.16, B.348 R, S 469(M + 1)+ Tab.16, B.349 R, S 478(M + 1)+ Tab.16, B.350 R, S 490(M + 1)+ Tab.16, B.351 R, S 493(M + 1)+ Tab.16, B.352 R, S 502(M + 1)+ Tab.16, B.353 R, S 512(M + 1)+ Tab.16, B.354 R, S 517(M + 1)+ Tab.16, B.355 R, S 518(M + 1)+ Tab.16, B.356 R, S 521(M + 1)+ Tab.16, B.357 R, S 535(M + 1)+ Tab.16, B.358 R, S 560(M + 1)+ Tab.16, B.362 R, S 493(M + 1)+ Tab.17, B.1 R oil Tab.17, B.3 R, S 123-128° C. Tab.17, B.3 R 126-127 Tab.17, B.3 S oil Tab.17, B.11 R oil Tab.17, B.79 R, S 144-145° C. Tab.17, B.82 R, S 115.5-117.5° C. Tab.17, B.85 R, S 139.5-140.5° C. Tab.17, B.88 R, S 96-97.5° C. Tab.17, B.91 R, S 461(M + 1)+ Tab.17, B.94 R, S 476(M + 1)+ Tab.17, B.248 R, S 507(M + 1)+ Tab.17, B.251 R, S 520(M − 1)−; 522(M + 1)+ Tab.17, B.258 R, S 489(M + 1)+ Tab.17, B.261 R, S 504(M + 1)+ Tab.17, B.273 R, S 480(M + 1)+ Tab.17, B.334 R, S 135-137° C. Tab.17, B.339 R, S 449(M + 1)+ Tab.17, B.340 R, S 451(M + 1)+ Tab.17, B.345 R, S 461(M + 1)+ Tab.17, B.346 R, S 461(M + 1)+ Tab.17, B.347 R, S 465(M + 1)+ Tab.17, B.348 R, S 467(M + 1)+ Tab.17, B.349 R, S 475(M + 1)+ Tab.17, B.350 R, S 488(M + 1)+ Tab.17, B.351 R, S 491(M + 1)+ Tab.17, B.352 R, S 500(M + 1)+ Tab.17, B.353 R, S 510(M + 1)+ Tab.17, B.354 R, S 515(M + 1)+ Tab.17, B.355 R, S 516(M + 1)+ Tab.17, B.356 R, S 519(M + 1)+ Tab.17, B.358 R, S 558(M + 1)+ Tab.17, B.359 R, S 435(M + 1)+ Tab.17, B.360 R, S 465(M + 1)+ Tab.17, B.361 R, S 476(M + 1)+ Tab.17, B.362 R, S 491(M + 1)+ Tab.17, B.363 R, S 500(M + 1)+ Tab.17, B.364 R, S 450(M + 1)+ Tab.17, B.365 R, S 464(M + 1)+ Tab.17, B.366 R, S 466(M + 1)+ Tab.17, B.367 R, S 476(M + 1)+ Tab.17, B.368 R, S 476(M + 1)+ Tab.17, B.369 R, S 480(M + 1)+ Tab.17, B.370 R, S 482(M + 1)+ Tab.17, B.371 R, S 490(M + 1)+ Tab.17, B.372 R, S 491(M + 1)+ Tab.17, B.373 R, S 506(M + 1)+ Tab.17, B.374 R, S 506(M + 1)+ Tab.17, B.375 R, S 515(M + 1)+ Tab.17, B.376 R, S 515(M + 1)+ Tab.17, B.377 R, S 525(M + 1)+ Tab.17, B.378 R, S 530(M + 1)+ Tab.17, B.379 R, S 531(M + 1)+ Tab.17, B.380 R, S 573(M + 1)+ Tab.18, B.3 diastereomere A 477(M − 1)− (rac.) Tab.18, B.3 diastereomere B 477(M − 1)− (rac.) Tab.18, B.38 R, S 130-132° C. Tab.18, B.85 R, S 141.5-143.5° C. / 459(M + 1)+ Tab.18, B.88 R, S 110.5-113.5° C. / 474(M + 1)+ Tab.18, B.319 R, S 161-163° C. Tab.20, B.3 R, S 140-143° C. Tab.21, B.3 R, S 121-123° C. Tab.21, B.88 R, S 119.5-121.5° C. Tab.21, B.91 R, S 489(M + 1)+ Tab.21, B.94 R, S 504(M + 1)+ Tab.21, B.258 R, S 517(M + 1)+ Tab.21, B.261 R, S 532(M + 1)+ Tab.21, B.319 R, S 110-112° C. Tab.21, B.334 R, S 127-128° C. Tab.21, B.339 R, S 477(M + 1)+ Tab.21, B.340 R, S 479(M + 1)+ Tab.21, B.345 R, S 489(M + 1)+ Tab.21, B.347 R, S 494(M + 1)+ Tab.21, B.348 R, S 495(M + 1)+ Tab.21, B.349 R, S 503(M + 1)+ Tab.21, B.351 R, S 519(M + 1)+ Tab.21, B.352 R, S 528(M + 1)+ Tab.21, B.353 R, S 538(M + 1)+ Tab.21, B.354 R, S 543(M + 1)+ Tab.21, B.355 R, S 544(M + 1)+ Tab.21, B.356 R, S 547(M + 1)+ Tab.21, B.358 R, S 586(M + 1)+ Tab.21, B.359 R, S 463(M + 1)+ Tab.21, B.361 R, S 504(M + 1)+ Tab.21, B.362 R, S 519(M + 1)+ Tab.21, B.363 R, S 528(M + 1)+ Tab.21, B.364 R, S 478(M + 1)+ Tab.21, B.365 R, S 492(M + 1)+ Tab.21, B.366 R, S 494(M + 1)+ Tab.21, B.367 R, S 504(M + 1)+ Tab.21, B.368 R, S 504(M + 1)+ Tab.21, B.369 R, S 509(M + 1)+ Tab.21, B.370 R, S 510(M + 1)+ Tab.21, B.371 R, S 518(M + 1)+ Tab.21, B.372 R, S 519(M + 1)+ Tab.21, B.373 R, S 534(M + 1)+ Tab.21, B.374 R, S 534(M + 1)+ Tab.21, B.376 R, S 543(M + 1)+ Tab.21, B.377 R, S 553(M + 1)+ Tab.21, B.378 R, S 558(M + 1)+ Tab.21, B.379 R, S 559(M + 1)+ Tab.21, B.381 R, S 562(M + 1)+ Tab.24, B.3 R, S 119-127° C. Tab.25, B.3 R, S 143-149° C. Tab.27, B.3 diastereomere A 587(M − 1)− (rac.) Tab.27, B.3 diastereomere B 587(M − 1)− (rac.) Tab.30, B.3 R, S oil Tab.30, B.334 R, S 135-137° C. Tab.32, B.3 R, S 142-144° C. Tab.32, B.334 R, S 156-157° C. Tab.36, B.3 R, S 171-178° C. Tab.40, B.3 R, S 151-158° C. Tab.47, B.3 R, S 145-147° C. Tab.48, B.3 R, S 156-158° C. Tab.49, B.3 R, S 144-148° C. Tab.50, B.3 R, S 123-126° C. (M(ESMS) = ion peaks in electrospray massspectrometry)

TABLE D Ugi intermediates (VI)

(Me means methyl) phys. data No. R₂ R₃ A B m.p. ° C. D1 H 4-Cl,3-F-phenyl —CH₂CH₂— 3,4-di-MeO-phenyl oil D2 H 4-Cl,3-CF₃-phenyl —CH₂CH₂— 3,4-di-MeO-phenyl oil D3 H 4-Cl,3-F-phenyl —CH₂CH₂— 4-n-butylO,3-MeO- 94-97 phenyl D4 H 3,4-di-Cl-phenyl —CH₂CH₂— 3,4-di-MeO-phenyl oil D5 H 4-Br-phenyl —CH₂CH₂— 3,4-di-MeO-phenyl oil D6 H 4-Me-phenyl —CH₂CH₂— 3,4-di-MeO-phenyl 95-97 D7 H 4-CF₃O-phenyl —CH₂CH₂— 3,4-di-MeO-phenyl oil D8 H 3,4-di-MeO-phenyl —CH₂CH₂— 3,4-di-MeO-phenyl oil D9 H 4-N(Me)₂-phenyl —CH₂CH₂— 3,4-di-MeO-phenyl oil D10 H 4-MeS-phenyl —CH₂CH₂— 3,4-di-MeO-phenyl 71-75 D11 H 3-Me-phenyl —CH₂CH₂— 3,4-di-MeO-phenyl oil D12 H 3-CF₃-phenyl —CH₂CH₂— 3,4-di-MeO-phenyl oil D13 H 4-PhO-phenyl —CH₂CH₂— 3,4-di-MeO-phenyl oil D14 H 4-EtO-phenyl —CH₂CH₂— 3,4-di-MeO-phenyl 100-102 D15 H 3,4-(OCH₂O)-phenyl —CH₂CH₂— 3,4-di-MeO-phenyl oil D16 H 4-Ph-phenyl —CH₂CH₂— 3,4-di-MeO-phenyl oil D17 H 4-i-propyl-phenyl —CH₂CH₂— 3,4-di-MeO-phenyl 87-91 D18 H 4-(COOMe)-phenyl —CH₂CH₂— 3,4-di-MeO-phenyl 99-101 D19 H 3,4-di-F-phenyl —CH₂CH₂— 3,4-di-MeO-phenyl oil D20 H 4-tert.butyl-phenyl —CH₂CH₂— 3,4-di-MeO-phenyl 83-87 D21 H 4-CN-phenyl —CH₂CH₂— 3,4-di-MeO-phenyl oil D22 H 3-Cl-phenyl —CH₂CH₂— 3,4-di-MeO-phenyl oil D23 H 1-naphthyl —CH₂CH₂— 3,4-di-MeO-phenyl oil D24 H 3,5-di-Cl-phenyl —CH₂CH₂— 3,4-di-MeO-phenyl oil D25 H 2-thienyl —CH₂CH₂— 3,4-di-MeO-phenyl oil D26 H 4-Cl-phenyl —CH₂CH₂— 3-MeO,4-propargylO- oil phenyl D27 H 2-furanyl —CH₂CH₂— 3,4-di-MeO-phenyl oil D28 H 4-Ph-phenyl —CH₂CH₂— 3-MeO,4-propargylO- oil phenyl D29 H 4-Cl-phenyl —CH(CH₃)CH₂— oil D30 H 4-Br-phenyl —CH₂CH₂— 3-MeO,4-propargylO- oil phenyl D31 H 4-Me-phenyl —CH₂CH₂— 3-MeO,4-propargylO- oil phenyl D32 H 4-Br-phenyl —CH₂CH₂— 3-MeO,4-(pent-2′-in-1′- oil yloxy)-phenyl D33 H 4-Me-phenyl —CH₂CH₂— 3-MeO,4-(pent-2′-in-1′- oil yloxy)-phenyl D34 H 2-naphthyl —CH₂CH₂— 3,4-di-MeO-phenyl oil D35 H 3,4-di-Cl-phenyl —CH₂CH₂— 3-MeO,4-propargylO- oil phenyl D36 H 4-Me-phenyl —CH(CH₃)CH₂— 3-MeO,4-propargylO- oil phenyl D37 H 5-Me,2-furanyl —CH₂CH₂— 3-MeO,4-allyO-phenyl oil D38 H 3-F-phenyl —CH₂CH₂— 3-MeO,4-allyO-phenyl oil D39 H 5-Me,2-thienyl —CH₂CH₂— 3-MeO,4-allyO-phenyl oil D40 H 4-MeO-phenyl —CH₂CH₂— 3-MeO,4-allyO-phenyl oil D41 H 2-MeO-phenyl —CH₂CH₂— 3-MeO,4-allyO-phenyl oil D42 H 3-Cl-phenyl —CH₂CH₂— 3-MeO,4-allyO-phenyl oil D43 H 2-Cl-phenyl —CH₂CH₂— 3-MeO,4-allyO-phenyl oil D44 H 3,5-di-F-phenyl —CH₂CH₂— 3-MeO,4-allyO-phenyl oil D45 H 3-Me,4-MeO-phenyl —CH₂CH₂— 3-MeO,4-allyO-phenyl oil D46 H 4-N-acetylamino-phenyl —CH₂CH₂— 3-MeO,4-allyO-phenyl oil D47 H 4-(COOMe)-phenyl —CH₂CH₂— 3-MeO,4-allyO-phenyl oil D48 H 3,5-di-MeO-phenyl —CH₂CH₂— 3-MeO,4-allyO-phenyl oil D49 H 2,4-di-MeO-phenyl —CH₂CH₂— 3-MeO,4-allyO-phenyl oil D50 H 2,4-di-Cl-phenyl —CH₂CH₂— 3-MeO,4-allyO-phenyl oil D51 H 3-(N-pyrrolidino)-phenyl —CH₂CH₂— 3-MeO,4-allyO-phenyl oil D52 H 4-Ph-phenyl —CH₂CH₂— 3-MeO,4-allyO-phenyl oil D53 H 3-Br-phenyl —CH₂CH₂— 3-MeO,4-allyO-phenyl oil D54 H 3-MeO,4-propargylO- —CH₂CH₂— 3-MeO,4-allyO-phenyl oil phenyl D55 H 3-Br,2-thienyl —CH₂CH₂— 3-MeO,4-allyO-phenyl oil D56 H 3-fluorenyl —CH₂CH₂— 3-MeO,4-allyO-phenyl oil D57 H 3-(4′-Cl—PhO)-phenyl —CH₂CH₂— 3-MeO,4-allyO-phenyl oil D58 H 5-Me,2-furanyl —CH₂CH₂— 3-MeO,4-propargylO- oil phenyl D59 H 3-F-phenyl —CH₂CH₂— 3-MeO,4-propargylO- oil phenyl D60 H 5-Me,2-thienyl —CH₂CH₂— 3-MeO,4-propargylO- oil phenyl D61 H 4-MeO-phenyl —CH₂CH₂— 3-MeO,4-propargylO- oil phenyl D62 H 2-MeO-phenyl —CH₂CH₂— 3-MeO,4-propargylO- oil phenyl D63 H 3-MeO-phenyl —CH₂CH₂— 3-MeO,4-propargylO- oil phenyl D64 H 3-Cl-phenyl —CH₂CH₂— 3-MeO,4-propargylO- oil phenyl D65 H 2-Cl-phenyl —CH₂CH₂— 3-MeO,4-propargylO- oil phenyl D66 H 3,5-di-F-phenyl —CH₂CH₂— 3-MeO,4-propargylO- oil phenyl D67 H 3-Me,4-MeO-phenyl —CH₂CH₂— 3-MeO,4-propargylO- oil phenyl D68 H 4-NO₂-phenyl —CH₂CH₂— 3-MeO,4-propargylO- oil phenyl D69 H 4-N-acetylamino-phenyl —CH₂CH₂— 3-MeO,4-propargylO- oil phenyl D70 H 4-(COOMe)-phenyl —CH₂CH₂— 3-MeO,4-propargylO- oil phenyl D71 H 3,5-di-MeO-phenyl —CH₂CH₂— 3-MeO,4-propargylO- oil phenyl D72 H 2,4-di-Cl-phenyl —CH₂CH₂— 3-MeO,4-propargylO- oil phenyl D73 H 4-(N-pyrrolidino)-phenyl —CH₂CH₂— 3-MeO,4-propargylO- oil phenyl D74 H 3-Br-phenyl —CH₂CH₂— 3-MeO,4-propargylO- oil phenyl D75 H 3-MeO,4-propargylO- —CH₂CH₂— 3-MeO,4-propargylO- oil phenyl phenyl D76 H 4-Br,2-thienyl —CH₂CH₂— 3-MeO,4-propargylO- oil phenyl D77 H 3-fluorenyl —CH₂CH₂— 3-MeO,4-propargylO- oil phenyl D78 H 4-(4′-Cl—PhO)-phenyl —CH₂CH₂— 3-MeO,4-propargylO- oil phenyl D79 H 2,4-di-MeO-phenyl —CH₂CH₂— 3-MeO,4-propargylO- oil phenyl D80 H 5-Me,2-furanyl —CH₂CH₂— 3-MeO,4-(pent-2′-in-1′- oil yloxy)-phenyl D81 H 3-F-phenyl —CH₂CH₂— 3-MeO,4-(pent-2′-in-1′- oil yloxy)-phenyl D82 H 5-Me,2-thienyl —CH₂CH₂— 3-MeO,4-(pent-2′-in-1′- oil yloxy)-phenyl D83 H 4-MeO-phenyl —CH₂CH₂— 3-MeO,4-(pent-2′-in-1′- oil yloxy)-phenyl D84 H 2-MeO-phenyl —CH₂CH₂— 3-MeO,4-(pent-2′-in-1′- oil yloxy)-phenyl D85 H 3-MeO-phenyl —CH₂CH₂— 3-MeO,4-(pent-2′-in-1′- oil yloxy)-phenyl D86 H 2-Cl-phenyl —CH₂CH₂— 3-MeO,4-(pent-2′-in-1′- oil yloxy)-phenyl D87 H 3,5-di-F-phenyl —CH₂CH₂— 3-MeO,4-(pent-2′-in-1′- oil yloxy)-phenyl D88 H 3-Me,4-MeO-phenyl —CH₂CH₂— 3-MeO,4-(pent-2′-in-1′- oil yloxy)-phenyl D89 H 4-NO₂-phenyl —CH₂CH₂— 3-MeO,4-(pent-2′-in-1′- oil yloxy)-phenyl D90 H 4-(COOMe)-phenyl —CH₂CH₂— 3-MeO,4-(pent-2′-in-1′- oil yloxy)-phenyl D91 H 3,5-di-MeO-phenyl —CH₂CH₂— 3-MeO,4-(pent-2′-in-1′- oil yloxy)-phenyl D92 HG 2,4-di-MeO-phenyl —CH₂CH₂— 3-MeO,4-(pent-2′-in-1′- oil yloxy)-phenyl D93 H 2,4-di-Cl-phenyl —CH₂CH₂— 3-MeO,4-(pent-2′-in-1′- oil yloxy)-phenyl D94 H 4-(N-pyrrolidino)-phenyl —CH₂CH₂— 3-MeO,4-(pent-2′-in-1′- oil yloxy)-phenyl D95 H 3-Br-phenyl —CH₂CH₂— 3-MeO,4-(pent-2′-in-1′- oil yloxy)-phenyl D96 H 3-MeO,4-propargylO- —CH₂CH₂— 3-MeO,4-(pent-2′-in-1′- oil phenyl yloxy)-phenyl D97 H 4-Br,2-thienyl —CH₂CH₂— 3-MeO,4-(pent-2′-in-1′- oil yloxy)-phenyl D98 H 3-fluorenyl —CH₂CH₂— 3-MeO,4-(pent-2′-in-1′- oil yloxy)-phenyl D99 H 4-(4′-Cl—PhO)-phenyl —CH₂CH₂— 3-MeO,4-(pent-2′-in-1′- oil yloxy)-phenyl D100 H 5-Me,2-furanyl —CH₂CH₂— 3,4-di-MeO-phenyl oil D101 H 3-F-phenyl —CH₂CH₂— 3,4-di-MeO-phenyl oil D102 H 5-Me,2-thienyl —CH₂CH₂— 3,4-di-MeO-phenyl oil D103 H 4-MeO-phenyl —CH₂CH₂— 3,4-di-MeO-phenyl oil D104 H 2-MeO-phenyl —CH₂CH₂— 3,4-di-MeO-phenyl oil D105 H 3-MeO-phenyl —CH₂CH₂— 3,4-di-MeO-phenyl oil D106 H 2-Cl-phenyl —CH₂CH₂— 3,4-di-MeO-phenyl oil D107 H 3,5-di-F-phenyl —CH₂CH₂— 3,4-di-MeO-phenyl oil D108 H 3-Me,4-MeO-phenyl —CH₂CH₂— 3,4-di-MeO-phenyl oil D109 H 4-NO₂-phenyl —CH₂CH₂— 3,4-di-MeO-phenyl oil D110 H 4-(N-acetylamino)- —CH₂CH₂— 3,4-di-MeO-phenyl oil phenyl D111 H 3,5-di-MeO-phenyl —CH₂CH₂— 3,4-di-MeO-phenyl oil D112 H 2,4-di-MeO-phenyl —CH₂CH₂— 3,4-di-MeO-phenyl oil D113 H 2,4-di-Cl-phenyl —CH₂CH₂— 3,4-di-MeO-phenyl oil D114 H 4-(N-pyrrolidino)-phenyl —CH₂CH₂— 3,4-di-MeO-phenyl oil D115 H 3-Br-phenyl —CH₂CH₂— 3,4-di-MeO-phenyl oil D116 H 3-MeO,4-propargylO- —CH₂CH₂— 3,4-di-MeO-phenyl oil phenyl D117 H 4-Br,2-thienyl —CH₂CH₂— 3,4-di-MeO-phenyl oil D118 H 3-fluorenyl —CH₂CH₂— 3,4-di-MeO-phenyl oil D119 H 4-(4′-Cl—PhO)-phenyl —CH₂CH₂— 3,4-di-MeO-phenyl oil

Formulation Examples for Compounds of Formula I

Working procedures for preparing formulations of the compounds of formula I such as Emulsifiable concentrates, Solutions, Granulates, Dusts and Wettable powders are described in WO 97/33890.

Biological Examples

B-1: Action Against Plasmopara Viticola on Vines

a) Residual-protective Action

Vine seedlings are sprayed at the 4- to 5-leaf stage with a spray mixture (0.02% active ingredient) prepared from a wettable powder formulation of the test compound. After 24 hours, the treated plants are infected with a sporangia suspension of the fungus. Fungus infestation is evaluated after incubation for 6 days at 95-100% relative humidity and 20° C.

b) Residual-curative Action

Vine seedlings are infected at the 4- to 5-leaf stage with a sporangia suspension of the fungus. After incubation for 24 hours in a humidity chamber at 95-100% relative humidity and 20° C., the infected plants are dried and sprayed with a spray mixture (0.02% active ingredient) prepared from a wettable powder formulation of the test compound. After the spray coating has dried, the treated plants are placed in the humidity chamber again. Fungus infestation is evaluated 6 days after infection.

Compounds of Tables 1 to 50 exhibit a very good fungicidal action against Plasmopara viticola on vines. Compounds Tab.14,B.203; Tab.14,B.319; Tab.14,B.335; Tab.14,B.336; Tab.15,B.3; Tab.17,B.1; Tab.17,B.3; Tab.17,B.82; Tab.17,B.88; Tab.17,B.251; Tab.21,B.3; Tab.21,B.88; Tab.21,B.319; Tab.24,B.3 and others virtually completely inhibit fungal infestation (0 to 10% infestation) in this test. On the other hand, Plasmopara infestation on untreated and infected control plants is 100%.

B-2: Action Against Phytophthora on Tomato Plants

a) Residual-protective Action

After a cultivation period of 3 weeks, tomato plants are sprayed with a spray mixture (0.02% active ingredient) prepared from a wettable powder formulation of the test compound. After 48 hours, the treated plants are infected with a sporangia suspension of the fungus. Fungus infestation is evaluated after incubation of the infected plants for 4 days at 90-100% relative humidity and 20° C.

b) Systemic Action

After a cultivation period of 3 weeks, tomato plants are watered with a spray mixture (0.02% active ingredient based on the volume of the soil) prepared from a wettable powder formulation of the test compound. Care is taken that the spray mixture does not come into contact with the parts of the plants which are above ground. After 4 days, the treated plants are infected with a sporangia suspension of the fungus. Fungus infestation is evaluated after incubation of the infected plants for 4days at 90-100% relative humidity and 20° C. Compounds of Tables 1 to 50 exhibit a lasting effect (less than 20% fungus infestation). Infestation is prevented virtually completely (0 to 5% infestation) with compounds Tab.14,B.1 12; Tab.14,B.203; Tab.14,B.335; Tab.14,B.336; Tab.15,B.3; Tab.17B.1; Tab.17,B.3; Tab.17,B.82; Tab.17,B.85; Tab.17,B.88; Tab.17,B.251; Tab.18,B.3; Tab.21,B.3; Tab.21,B.88; Tab.21,B.319 and others. On the other hand, Phytophthora infestation on untreated and infected control plants is 100%.

B-3 Action Against Phytophthora on Potato Plants

a) Residual-protective Action

2-3 week old potato plants (Bintje variety) are sprayed with a spray mixture (0.02% active ingredient) prepared from a wettable powder formulation of the test compound. After 48 hours, the treated plants are infected with a sporangia suspension of the fungus. Fungus infestation is evaluated after incubation of the infected plants for 4 days at 90-100% relative humidity and 20° C.

b) Systemic Action

2-3 week old potato plants (Bintje variety) are watered with a spray mixture (0.02% active ingredient based on the volume of the soil) prepared from a wettable powder formulation of the test compound. Care is taken that the spray mixture does not come into contact with the parts of the plants which are above ground. After 48 hours, the treated plants are infected with a sporangia suspension of the fungus. Fungus infestation is evaluated after incubation of the infected plants for 4 days at 90-100% relative humidity and 20° C. Compounds of Tables 1 to 50 exhibit a lasting effect (less than 20% fungus infestation). Infestation is prevented virtually completely (0 to 5% infestation) with compounds Tab.14,B.38; Tab.14,B.203; Tab.14,B.319; Tab.15,B.3; Tab.17,B.1; Tab.17,B.3; Tab.17,B.82; Tab.17,B.85; Tab.17,B.88; Tab.17,B.251 and others. On the other hand, Phytophthora infestation on untreated and infected control plants is 100%. 

What is claimed is:
 1. A compound of formula I

wherein n is the number zero or one; R₁ is optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl; or a group NR_(a)R_(b) wherein R_(a) and R_(b) are each independently of the other hydrogen, alkyl or form together an alkylene bridge; R₂ is hydrogen or alkyl; R₃ is optionally substituted aryl or heteroaryl; A is alkylene; and B is optionally substituted aryl; with the exception of the following compounds 2-phenyl-N-(1-phenyl-ethyl)-2-(4-aminophenyl)-sulfonylamino-acetamide, 2-phenyl-N-(1-phenyl-ethyl)-2-(4-methylphenyl)-sulfonylamino-acetamide, 2-phenyl-N-(1-phenyl-ethyl)-2-(4-chlorophenyl)-sulfonylamino-acetamide, 2-phenyl-N-(1-phenyl-ethyl)-2-(4-nitrophenyl)-sulfonylamino-acetamide, 2-phenyl-N-(1-phenyl-ethyl)-2-(4-methoxyphenyl)-sulfonylamino-acetamide, 2-phenyl-N-(1-phenyl-ethyl)-2-(4-fluorophenyl)-sulfonylamino-acetamide, 2-phenyl-N-(1-phenyl-ethyl)-2-phenyl-sulfonylamino-acetamide and 2-phenyl-N-(1-phenyl-ethyl)-2-methane-sulfonylamino-acetamide.
 2. A compound of formula I according to claim 1, wherein n is the number zero or one; R₁ is C₁-C₁₀alkyl, C₂-C₁₀alkenyl, C₂-C₁₀alkynyl, C₃-C₈cycloalkyl, C₃-C₈cycloalkyl-C₁-C₆alkyl, C₁-C₁₀aryl, or C₆-C₁₀aryl-C₁-C₆alkyl that are optionally mono- or poly-substituted by C₁-C₈alkyl, C₁-C₈alkoxy, C₁-C₈alkylthio, C₁-C₈alkylsulfonyl, C₃-C₈cycloalkyl, C₁-C₈alkoxycarbonyl, C₃-C₈alkenyloxycarbonyl, C₃-C₈alkynyloxycarbonyl, C₃-C₈cycloalkyl-C₁-C₆alkyl, C₂-C₈alkenyl, C₂-C₈alkynyl, C₃-C₈alkenyloxy, C₃-C₈alkynyloxy, C₁-C₈alkanoyl (where all these alkyl, alkenyl, alkynyl or cycloalkyl containing groups may be partially or fully halogenated), halogen, cyano or nitro; or a group NR_(a)R_(b), wherein R_(a) and R_(b) are each independently of the other hydrogen, C₁-C₈alkyl or together are C₂-C₇alkylen; R₂ is hydrogen or C₁-C₈alkyl; R₃ is phenyl, naphthyl or heteroaryl formed by 1 or 2 five- or six-membered rings containing 1 to 4 identical or different heteroatoms selected from oxygen, nitrogen or sulfur and are optionally mono- or poly-substituted by C₁-C₈alkyl, C₂-C₈alkenyl, C₂-C₈alkynyl, C₁-C₈alkoxy, C₁-C₈alkylthio, C₁-C₈alkylsulfonyl, C₃-C₈cycloalkyl, C₃-C₈cycloalkyl-C₁-C₆alkyl, C₁-C₈alkoxycarbonyl, C₃-C₈alkenyloxycarbonyl, C₃-C₈alkynyloxycarbonyl, C₁-C₄alkylendioxy, C₃-C₈cycloalkyloxy, C₃-C₈alkenyloxy, C₃-C₈alkynyloxy, C₁-C₈alkanoyl, C₁-C₈dialkylamino, C₁-C₈alkylamino (where all these alkyl alkenyl, alkynyl or cycloalkyl containing groups may be partially or fully halogenated), halogen, nitro, cyano, hydroxy or amino; A is C₁-C₈alkylen; and B is phenyl optionally mono- or poly-substituted by C₁-C₈alkyl, C₂-C₈alkenyl, C₂-C₈alkynyl, C₁-C₈alkoxy, C₁-C₈alkylthio, C₁-C₈alkylsulfonyl, C₃-C₈cycloalkyl, C₃-C₈cycloalkyl-C₁-C₆alkyl, C₁-C₈alkoxycarbonyl, C₃-C₈alkenyloxycarbonyl, C₃-C₈alkynyloxycarbonyl, C₃-C₈cycloalkyloxy, C₃-C₈alkenyloxy, C₃-C₈alkynyloxy, C₁-C₈alkanoyl, C₁-C₈dialkylamino, C₁-C₈alkylamino, C₆-C₁₀aryloxy, C₆-C₁₀aryl-C₁-C₆alkoxy, C₆-C₁₀aryl-C₁-C₆alkenyloxy, C₆-C₁₀aryl-C₁-C₆alkynyloxy, C₁-C₈alkanoyloxy (where all these alkyl alkenyl, alkynyl or cycloalkyl containing groups may be partially or fully halogenated and where all aryl containing groups may be optionally mono- or poly-substituted by C₁-C₈alkyl, C₂-C₈alkenyl C₃-C₈cycloalkyl, C₁-C₈alkoxy, C₁-C₈alkylthio, C₁-C₈alkoxycarbonyl C₁-C₈halogenalkyl, C₁-C₈halogenalkoxy, C₁-C₈halogenthioalkyl, halogen nitro or cyano), halogen, nitro, cyano, hydroxy, amino or the phenyl group may be substituted in two adjacent positions by C₁-C₄alkylenedioxy wherein the alkylene part may be substituted by halogen.
 3. A compound of formula I according to claim 2, wherein n is the number zero or one; R₁ is C₁-C₁₀alkyl C₂-C₁₀alkenyl, C₃-C₈cycloalkyl that are optionally mono- or poly-substituted by C₁-C₈alkyl, C₁-C₈alkoxy, C₁-C₈alkylthio, C₁-C₈alkanoyl, C₁-C₈alkoxycarbonyl, C₁-C₈halogenalkyl, C₁-C₈halogenalkoxy, C₁-C₈halogenalkylthio, halogen, nitro or cyano; or a group NR_(a)R_(b), wherein R_(a) and R_(b) are each independently of the other hydrogen, C₁-C₈alkyl, or together are tetramethylene or pentamethylene; R₂ is hydrogen or methyl; R₃ is phenyl, naphthyl, furyl, thienyl, imidazolyl, thiazolyl, oxazolyl, pyridyl, pyrimidinyl, benzothiophenyl, benzothiazolyl, chinolinyl, pyrazolyl, indolyl, benzimidazolyl or pyrrolyl optionally substituted by 1 to 3 substituents selected from C₁-C₈alkyl, C₂-C₈alkenyl, C₃-C₈cycloalkyl, C₁-C₈alkoxy, C₁-C₈alkylthio, C₁-C₈alkoxycarbonyl, C₁-C₈halogenalkyl, C₁-C₈halogenalkoxy, C₁-C₈halogenalkylthio, halogen, hydroxy, nitro or cyano; A is C₁-C₄alkylen; and B is phenyl optionally substituted by 1 to 3 substituents selected from C₁-C₈alkyl, C₁-C₈alkoxy, C₃-C₈alkenyloxy, C₃-C₈alkynyloxy, phenyl-C₁-C₆alkyloxy, phenyl-C₃-C₆alkenyloxy, phenyl-C₃-C₆alkynyloxy, C₁-C₈alkylthio, C₁-C₈alkoxycarbonyl, C₁-C₈halogenalkoxy, C₃-C₈halogenalkenyloxy, halogen, hydroxy, nitro or cyano (where all phenyl containing groups may be optionally substituted by 1 to 3 substituents selected from C₁-C₈alkyl, C₁-C₈alkoxy, C₁-C₈alkylthio, C₁-C₈halogenalkyl, C₁-C₈halogenalkoxy, C₁-C₈halogenthioalkyl, halogen or cyano).
 4. A compound of formula I according to claim 3, wherein n is the number one; R₁ is C₁-C₆alkyl, C₂-C₁₀alkenyl, C₅-C₆cycloalkyl, that are optionally mono- or poly-substituted by C₁-C₈alkyl, C₁-C₈alkoxy, C₁-C₈alkoxycarbonyl, C₁-C₈halogenalkyl, C₁-C₈halogenalkoxy, halogen or cyano; or a group NR_(a)R_(b), wherein R_(a) and R_(b) are each independently of the other methyl or ethyl; R₂ is hydrogen; R₃ is phenyl optionally substituted by 1 to 3 substituents selected from C₁-C₈alkyl, C₂-C₈alkenyl, C₃-C₈cycloalkyl, C₁-C₈alkoxy, C₁-C₈alkylthio, C₁-C₈alkoxycarbonyl, C₁-C₈halogenalkyl, C₁-C₈halogenalkoxy, C₁-C₈halogenthioalkyl, halogen, hydroxy, nitro or cyano; A is ethylen; and B is phenyl optionally substituted by 2 to 3 substituents selected from C₁-C₈alkyl, C₁-C₈alkoxy, C₃-C₈alkenyloxy, C₃-C₈alkynyloxy, phenyl-C₁-C₆alkyloxy, phenyl-C₃-C₆alkenyloxy, phenyl-C₃-C₆alkynyloxy, C₁-C₈alkylthio, C₁-C₈alkoxycarbonyl, C₁-C₈halogenalkoxy, C₃-C₈halogenalkenyloxy, halogen, hydroxy, nitro or cyano (where all phenyl containing groups may be optionally substituted by 1 to 3 substituents selected from C₁-C₈alkyl, C₁-C₈alkoxy, C₁-C₈alkylthio, C₁-C₈halogenalkyl, C₁-C₈halogenalkoxy, C₁-C₈halogenthioalkyl, halogen or cyano).
 5. A compound of formula I according to claim 4, wherein n is the number one; R₁ is C₁-C₄alkyl optionally mono- or poly-substituted by fluorine, chlorine, bromine or dimethylamin; R₂ is hydrogen; R₃ is phenyl optionally substituted by 1 to 3 substituents selected from C₁-C₈alkyl, C₂-C₈alkenyl, C₃-C₈cycloalkyl, C₁-C₈alkoxy, C₁-C₈alkylthio, C₁-C₈alkoxycarbonyl, C₁-C₈halogenalkyl, C₁-C₈halogenalkoxy, C₁-C₈halogenthioalkyl, halogen, nitro or cyano; A is ethylen; and B is a group

 wherein R₈ is C₁-C₄alkyl, and R₉ is C₁-C₈alkyl, C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl-C₁-C₆alkyl, phenyl-C₃-C₆alkenyl, phenyl-C₃-C₆alkynyl, C₁-C₈halogenalkyl, C₃-C₈halogenalkenyl (where all phenyl containing groups may be optionally substituted by 1 to 3 substituents selected from C₁-C₈alkyl, C₁-C₈alkoxy, C₁-C₈alkylthio, C₁-C₈halogenalkyl, C₁-C₈halogenalkoxy, C₁-C₈halogenthioalkyl, halogen or cyano).
 6. A process for the preparation of a compound of formula I according to claim 1, which comprises a) reacting an amino acid of formula II or a carboxy-activated derivative of an amino acid of formula II

 with an amine of the formula V H₂N———A———B  (V); or b) reacting a sulfonyl halide or sulfinyl halide of formula III

where X is halide, with an amino acid derivative of formula VI

 and optionally c) oxidizing a compound of formula I wherein n=0 and wherein R₁, R₂, R₃, A and B have the meaning as defined for formula I to a compound of formula I wherein n=1.
 7. A composition for controlling and preventing infestation of plants by microorganisms, which comprises as active ingredient a compound of formula I according to claim 1, together with a suitable carrier.
 8. A method of controlling and preventing infestation of plants by microorganisms, which comprises applying a compound of formula I according to claim 1 as active ingredient to the plant, to parts of the plant or to the nutrient medium of the plant.
 9. A method according to claim 8, which comprises treating seed.
 10. The intermediate of formula VI

wherein R₂, R₃, A and B are as defined in formula I.
 11. A process for the preparation of a compound of formula VI according to claim 10, which comprises d) hydrolizing a compound of formula X

 under acidic or basic conditions at a temperature between 0° and 100° C., wherein R₂, R₃, A and B have the meaning as defined for formula I and wherein R₁₀ is lower alkyl or hydrogen. 